Eric opens up about his early failures, including his time at there.com, a virtual world startup that had everything going for it except customers. That painful experience led him to co-found IMVU, where he began experimenting with rapid iteration, minimum viable products, and data driven decision making, the core principles that would eventually become the Lean Startup.

The conversation takes a sharp turn into today's AI driven world, where Eric offers a refreshingly candid and cautionary perspective. While he acknowledges that AI tools like Claude Code have made it faster and cheaper than ever to build and launch products, he warns that founders are falling into a dangerous trap he calls "dark flow," mindlessly generating code and demos without actually learning, testing, or getting real customer feedback. He argues that the MVP is not the artifact itself, but the experiment and the learning that comes from it.

Eric also raises serious concerns about vibe coding, the practice of using AI to generate software that even its creators don't fully understand. He believes this is a ticking time bomb that could lead to a Chernobyl style disaster when AI generated, unreviewable code finds its way into mission critical applications.

The episode also covers the state of venture capital in the enterprise AI space, where Eric sees echoes of the dot com bubble, with enormous wealth being generated alongside questionable value creation. He shares his thoughts on OpenAI vs. Anthropic, the future of SaaS, the robotaxi wars, and why he still doesn't understand what Bitcoin is actually for.

Eric closes with a preview of his new book, Incorruptible, available May 26th, which digs deeper into principled entrepreneurship and long term thinking in business. Whether you're a first time founder or a seasoned investor, this episode is packed with hard won wisdom from one of Silicon Valley's most thoughtful voices.

In this episode of the FLF Skin in the Game Podcast, Saxon sits down with Abe Smith, Silicon Valley veteran, LP at Florida Funders, and one of the most globally experienced operators in enterprise SaaS to unpack the wild ride of building some of the most iconic tech companies of the last 25 years. From joining WebEx before Cisco's record-breaking $3.2B acquisition, to looking Eric Yuan in the eye and promising $1B in international revenue at Zoom (and delivering it in 18 months thanks to a little thing called COVID), Abe's stories are the kind you don't usually hear from the inside.

They also get into what made Zoom's culture so different, why Silicon Valley still matters, what it takes to spot a real founder, and the big one whether the next generational AI company can be built right here in Florida.

If you're a founder, investor, or just someone who loves a great business story, this one's for you.

🎙️ Subscribe, like, and share and if you're building something special, you know who to call.

Brian’s story begins just outside Washington, D.C., where he grew up as the oldest of three brothers in a disciplined and competitive household. His middle brother, Mack Hollins, famously received no college football offers, walked on at UNC, and went on to build a nine-year NFL career that includes a Super Bowl championship. His youngest brother served in the Marines. That foundation of resilience, accountability, and high standards continues to shape Brian’s approach to leadership and investing.

The conversation traces his path from Stanford, where a culture of ambition and innovation pushes students to think boldly, to Goldman Sachs, where he helped build the Emerging Entrepreneurs Coverage Group. During that time, he learned how to create real value for founders before ever writing a check, including early work supporting companies like Plaid. Those experiences laid the groundwork for how he thinks about venture capital today.

Brian also explains why he approached business school intentionally, using it as a strategic platform to build relationships and lay the foundation for launching Collide Capital. The discussion highlights the difference between raising a fund and building a firm, and what it takes to earn long-term institutional LP support.

The episode concludes with a look at Collide Capital’s investment focus on fintech infrastructure, supply chain and logistics, and the future of Gen Z in the workforce and why the best founders are relentlessly focused on solving one core problem.

A thoughtful and candid discussion on building with intention and playing the long game. Tune in to this episode. You don’t want to miss this one!

Suneera also shares about founding CEO School, a podcast and platform giving women the "Have-It-All" formula to scale like real CEOs, and offers some secrets as to why second-time founders move faster. They discuss how AI can enable leaner teams with outsize output and zero in on why Suneera remains deeply passionate about building in Florida.

Felix’s story starts long before hedge funds and venture capital. He moved to the U.S. from Germany during the 2008 financial crisis, initially planning to stay for just a year. That plan changed quickly. Early exposure to markets, coding, and emerging technology led him down a path of trading, crypto infrastructure, and eventually founding his own firm and launching Hartmann Capital the same day he signed his first apartment lease.

A major theme throughout the episode is conviction through firsthand experience. Felix doesn’t invest from a distance. He tests products, uses them extensively, and looks for signals that can’t be captured in a pitch deck. Whether it’s VR games, smart glasses, or brain computer interface technology, he believes the clearest insight comes from being a real user and understanding how a product fits into daily life.

The conversation explores why Felix shifted away from liquid crypto trading and toward long-term venture investing in frontier categories like VR, spatial computing, wearables, and neural interfaces. He explains how hardware limitations slowed VR adoption, why smart glasses may be closer to a breakout moment, and how enterprise use cases often precede consumer adoption. The discussion also touches on sub-vocal communication technology that allows people to interact with devices without speaking out loud and why it could fundamentally change how humans interface with machines.

Saxon and Felix also discuss the realities of investing on the “bleeding edge,” where traditional metrics don’t exist and patience is required. Felix breaks down how power-law outcomes often come from non-consensus bets and why underfunded categories tend to attract the most mission-driven founders.

The episode closes with reflections on geography, talent, and ecosystem building from Florida’s role in capital formation to the continued importance of Silicon Valley and Los Angeles for early-stage innovation.

The conversation dives into how Alumni Ventures approaches investing without leading rounds, instead partnering alongside top-tier venture firms while leveraging a global network of investors, operators, and founders. Mike explains how this “connected capital” model creates value beyond the check and why collaboration, rather than competition, is core to the firm’s strategy.

We also touch on broader trends shaping the future of venture capital, including artificial intelligence, energy innovation, healthcare, and the globalization of entrepreneurship. Drawing on decades of experience as both an operator and investor, Mike offers a thoughtful perspective on long-term thinking, governance, and what truly drives successful outcomes in venture backed companies.

This episode offers a behind-the-scenes look at a modern VC model, with insights that are relevant for founders, investors, and anyone curious about where innovation and capital are headed next.

Andrew shared how he launched Franklin Street at 26 and grew it into a full ecosystem of real estate services from capital markets and leasing to insurance and property management. He talks about why diversified revenue streams matter, especially in industries that ebb and flow with economic cycles.

We also unpacked today’s commercial real estate environment. Andrew describes the moment as a “rain delay” transactions are slow, liquidity is tight, and valuations are still adjusting after rapid interest-rate hikes. Even so, Florida remains uniquely strong thanks to continued population and capital migration. As lenders start pushing stalled assets toward resolution, he believes new opportunities will emerge.

Beyond market trends, Andrew shared insights on scaling teams, building culture, and developing young talent. His emphasis on authenticity, mentorship, and long-term potential over static skill sets is a refreshing and realistic take on leadership today.

We also explored the future of Westshore, including transportation needs, density, and how thoughtful planning could unlock the next phase of growth for the district. Add in his perspective on AI’s impact on real estate operations, and this episode covers a ton of ground.

If you're interested in real estate, leadership, or Tampa’s economic evolution, this is a must-listen.

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Andrew’s story begins with a need familiar to many families: his grandfather simply needed a little help and a little company. Instead of relying on the traditional caregiving model, Andrew wondered, What if we could make companionship more accessible, more human, and more joyful? That question became the foundation for Papa, a platform connecting older adults with “Papa Pals,” a modern, community-driven approach he perfectly describes as “grandkids on demand.”

In the episode, Andrew walks us through the early days of the idea, how he tested the concept, what he got wrong, and the surprising ways people responded. He opens up about the challenges of building a company in a space where emotional connection matters as much as logistics, as well as the pressure and responsibility that come with serving some of the most vulnerable members of our communities.

You’ll hear how Papa navigated fast growth, shifting market conditions, and the complexities of working with major health plans. Andrew also shares what he’s learned about leadership, resilience, and why the “kindness economy” may be the next frontier for healthcare innovation. His insights offer value not only to founders and operators, but to anyone curious about how a mission-driven business can scale without losing its heart.

This episode is a reminder that groundbreaking companies don’t always come from flashy tech or radical disruption, they’re often built from empathy, lived experience, and a desire to solve real problems for real people. Andrew’s journey proves that when you focus on creating meaningful human connections, the impact can reach far beyond what you imagined.

If you’re interested in aging, healthcare innovation, founder stories, or simply love hearing how a small spark can turn into something transformative, this is an episode you won’t want to miss.

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Eric emphasizes that great founders “look like anyone and come from anywhere.” While Silicon Valley has historically dominated the venture ecosystem, he notes that secondary and tertiary markets are now producing founders just as capable, thanks to the democratization of knowledge via the internet. Eric also points out a subtle but important distinction: founders from Silicon Valley often carry a relentless “grow fast, break things” mentality that accelerates execution, yet this mindset is increasingly being adopted across the country.

Hustle Fund takes a unique approach to investing, prioritizing hustle and execution over pedigree. Eric shares stories of candidates and founders who defied traditional expectations, one high school dropout who became a 100x operator, and a Princeton-educated engineer who couldn’t deliver. For Eric and his team, pre-seed investing is akin to hiring: it’s about identifying grit, determination, and the ability to learn quickly. Hustle Fund typically writes initial checks of $150,000 and pairs founders with growth projects and mentors to test their capabilities. About 20% of these teams receive a follow-up investment of $200,000. This model allows Hustle Fund to support hundreds of founders while remaining valuation-conscious.

Eric also highlights the influence of founders’ backgrounds, particularly in the service industry. Experiences as bartenders, waitstaff, or customer service agents cultivate resilience, emotional intelligence, and sales skills qualities that translate into startup success. For Eric, this aligns perfectly with the fund’s philosophy of backing “hustlers,” regardless of formal credentials or pedigree.

The conversation also dives into the role of media in venture capital. Eric explains how Hustle Fund leverages newsletters, events, and founder communities to provide value beyond capital, helping founders generate awareness, mentorship, and early revenue. This approach reflects the evolution of venture investing from a purely financial transaction to a hands-on, service-oriented partnership.

Finally, Eric shares insights into managing an expansive portfolio of 620 companies across four funds. Hustle Fund uses sophisticated data systems and a network of mentors to track growth, assess progress, and double down on top performers efficiently.

Reflecting on the culture of failure in Silicon Valley, Eric notes that “When someone starts a company here and it doesn’t work out, the first question isn’t, ‘Why did you fail?’ but, ‘What did you learn, and when will you try again?’” This mindset, he believes, is essential for innovation and entrepreneurship.

This episode offers an invaluable look at what it takes to succeed as a founder and investor in today’s pre-seed ecosystem, highlighting hustle, resilience, and the evolving dynamics of venture capital.

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They talk about what it really means to bootstrap a company, the sleepless nights and skepticism they faced early on, and how they turned a beat-up cargo van into a viral, multi-million-dollar business. Along the way, they share how franchising became both their greatest challenge and smartest growth strategy, why brand and PR were everything, and the lessons they learned about scaling people, culture, and systems.

The conversation dives deep into Tampa’s rise as an entrepreneurial hub and why they believe the city’s collaborative spirit gives it a unique edge. They also open up about the evolution of Trash Butler, how raising outside capital differed from their bootstrapped journey, and what it’s really like answering to a board after running their own show for so long.

This episode is full of entrepreneurial wisdom, gritty stories, and quotable one-liners—from “teams win championships, families watch them” to “bootstrapping is the MBA, raising capital is the rocket fuel.”

If you’re an entrepreneur, investor, or simply curious about what it takes to build enduring businesses from the ground up, this conversation with Nick and Omar is a masterclass you won’t want to miss.

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Roger didn’t come from the startup world. He spent nearly two decades on Wall Street, running billion-dollar trading desks at Citi and Deutsche Bank. From the outside, it looked like a career anyone would want — but for Roger, it had run its course. Tired of internal politics and craving something more entrepreneurial, he walked away. Around the same time, he’d been dabbling in angel investing on the side. That small experiment — backing builders before product-market fit — quickly turned into a full-time obsession.

He began writing a blog, Information Arbitrage, to share his thinking publicly. The blog gained traction. Founders started reaching out. Other investors began to follow his thesis. At a time when the idea of a “New York tech ecosystem” was almost laughable, Roger had the clarity to see where it could go — and the conviction to act. By early 2010, he scraped together a $17 million first close. That first fund would eventually land at $50 million, and IA Ventures was born.

But the money was only part of the story. What set Roger apart then — and still does — is how early he’s willing to go. He prefers backing companies before the market even knows they exist. In fact, he often writes the first check before there’s a line of code written. This isn’t blind optimism. It’s founder-first investing grounded in deep research and sharp intuition.

Roger’s track record speaks for itself. He was an early backer of The Trade Desk when it was just a deck. He seeded Datadog, TubeMogul, and multiple other companies before they became category leaders. The common thread? Founders who could not only see the future but build their way into it. To Roger, great founders share something intangible: what he calls “aesthetic and empathy.”

“Great founders understand where their product stops and where the customer starts,” he said. That could mean designing APIs that developers love or building consumer apps that feel inevitable. Either way, the best founders have an intuitive sense of product, user behavior, and market timing. Roger knows how to find them — or maybe, they know how to find him. That’s the power of publishing, he says. His blog didn’t just clarify his thesis — it attracted the right people. It helped him raise a fund when few believed in early-stage investing outside Silicon Valley.

Since then, IA Ventures has grown to four funds and backed dozens of successful startups. Roger has since passed the torch to his partners and launched his next chapter: Eberg Capital. Now, he invests alongside his sons in a new wave of innovation — spanning sports, media, entertainment, and the evolving world of fandom.

But whether he’s backing a Marlins ownership stake, investing in Formula 1, or writing angel checks to creator economy startups, one thing hasn’t changed: Roger Ehrenberg still goes early. He still backs founders before the world sees their potential. And more often than not, he’s right.

Listen to the full episode with Roger Ehrenberg now.

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He dives into the early challenges of startup life, why his time at BCG taught him how to build for the enterprise, and how a Sunday football lineup and a conversation with a DraftKings exec sparked the idea behind Extend. What started as a playful concept around insuring fantasy sports lineups evolved into a fast-scaling company that now partners with major brands like Peloton and Brilliant Earth.

Rohan gets candid about raising $260M from SoftBank during the ZIRP era, making hard calls early, and steering Extend toward profitability.

Whether you’re a founder, investor, or just love a great startup story—this one’s worth a listen.

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KnowBe4, headquartered in Clearwater, Florida, is a cybersecurity training company focused on mitigating human risk through simulated phishing, user training, and real-time alerts. Today, it generates over $500 million in annual recurring revenue (ARR)—but it started in a 10x10 office, with no external funding.

Stu breaks down how he identified a massive market gap: most cyberattacks aren’t due to software vulnerabilities—they’re the result of social engineering and human error.

He shares how ransomware attacks in 2013 created a turning point for KnowBe4, propelling the startup into hypergrowth. His strategy? Move fast, market smart, and keep the product simple and sticky.

Stu also dives into:

• The future of SaaS in the age of AI
• How KnowBe4 is evolving into a platform company
• Why AI and quantum computing will trigger “company extinction events”
• His belief that LLMs are already a commodity, and the future lies in vertical AI agents

For founders and VCs alike, the episode offers a wealth of insights on startup scaling, product-market fit, and what investors should look for in repeat entrepreneurs.

Whether you're a founder, cybersecurity professional, or angel investor, this conversation with Stu Sjouwerman is a must-listen.

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From Goldman Sachs to Running Her Own VC Fund, Jenny’s journey into venture capital wasn’t linear. After growing up in New York City, attending Horace Mann, and studying at Penn, she began her career in investment management at Goldman Sachs. But she quickly realized that traditional finance wasn’t for her and pivoted to the startup world, joining MiniBar Delivery, a liquor marketplace. This hands-on tech experience gave her the edge she needed to transition into venture capital.

While pursuing her MBA at Columbia Business School, Jenny networked relentlessly, eventually landing a role at ENIAC Ventures, a leading seed-stage VC firm. She later joined Supernode Ventures, where she helped raise their first institutional fund. During the pandemic, she took a leap of faith and launched Four Acres Capital as a solo GP, giving her full control over investments and fund strategy. Tune in to hear the full episode.

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Clint’s journey into space tech started with a winding road through optical satellites and Earth observation, ultimately leading to NUVIEW and a game-changing focus on space-based LiDAR. LiDAR technology uses lasers to measure distances with astonishing precision, but until now, it’s mostly been limited to airplanes and drones, covering small areas. NUVIEW is taking it global—literally—by putting this technology into satellites to collect data on a planetary scale.

Clint doesn’t just see LiDAR as a tool for Earth. With NUVIEW’s recent selection for a European Space Agency mission to map the moon, the company is helping humanity take its next big step toward understanding and utilizing space.

This episode isn't just about LiDAR. Clint offers his insights on the state of the space industry, comparing it to “the first inning, bases loaded, no outs.” He highlights Florida’s growing role as a hub for aerospace innovation and discusses how companies like SpaceX have completely reshaped the game.

From revolutionizing Earth data collection to mapping the moon, NUVIEW’s story is a testament to how the space frontier is becoming more accessible and practical than ever before. Tune in to this fascinating conversation and catch a glimpse of the future

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Brent reflected on his experience leading companies like Allergan and Bausch & Lomb, where he navigated complex mergers and acquisitions totaling nearly $300 billion. His approach centers on aligning deals with a strong strategic rationale and financial discipline, ensuring long-term value creation rather than short-term gains.

A recurring theme throughout the conversation was Brent’s passion for leveraging technology to tackle inefficiencies in healthcare. He highlighted the potential of AI to transform drug discovery and streamline clinical trials, sharing how his company uses AI to identify solutions for challenging diseases. Brent also emphasized the need for universal, portable medical records to improve patient outcomes and reduce systemic inefficiencies—a vision that remains elusive but vital for the future.

As an active investor, Brent shared his enthusiasm for backing startups that prioritize innovation and have strong, experienced teams. He cited Roam, a Miami-based tech startup led by Howard Lerman, as an example of a company combining cutting-edge ideas with proven leadership. Brent underscored the value of working with founders who have “climbed the hill before,” noting that their experience and resilience often set them apart.

Looking to the future, Brent offered predictions on market trends, including the growing influence of AI and the expected resurgence in mergers and acquisitions as regulatory conditions evolve. His optimism about technological advancements was balanced by a thoughtful caution regarding overuse in areas like pharmaceuticals, emphasizing the importance of weighing benefits against risks.

The episode was not just a window into Brent’s accomplishments but also a reminder of the power of innovation, the importance of adaptability, and the need to continually refine one’s craft. For anyone navigating the intersection of technology, business, and leadership, Brent’s insights provide both inspiration and actionable guidance.

Be sure to tune in to Skin in the Game VC for more conversations with trailblazing leaders and investors shaping the future.

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Amy Wu, founder of Manifest, and Shannon Wu, founder of Open Home, have both built groundbreaking companies leveraging the transformative potential of AI. Manifest addresses Gen Z’s mental health challenges through personalized, AI-driven tools, creating bite-sized wellness interactions to combat loneliness and anxiety. Meanwhile, Open Home is revolutionizing smart speakers, enabling more intuitive and seamless voice interactions across a wide range of devices. Both sisters emphasized how AI allows lean teams to achieve significant impact, unlocking personalized solutions that enhance human connection and creativity.

Their journey reflects a shared commitment to innovation and a deep bond that has guided them through challenges and triumphs. They credit their early experiences at Stanford and the personalized support from Florida Funders as key drivers of their success. Florida Funders’ hands-on approach contrasts with the broader yet less personal resources of larger VC firms, offering a uniquely curated experience that has helped Amy and Shannon thrive.

As these visionary founders continue to push boundaries, their work underscores the exciting potential of AI and the importance of fostering meaningful human connections in an increasingly digital world. Startups like Manifest and Open Home showcase how technology can be a tool for empowerment, solving real-world challenges with creativity and purpose. Tune in to this latest episode of Skin in the Game.

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Ann’s professional journey began at Goldman Sachs, where she specialized in leveraged buyouts. Her transition to private equity allowed her to lead as a CEO, navigating a hospitality portfolio company through the COVID-19 crisis. This experience solidified her love for operational leadership and reshaped her investment philosophy. Ann now focuses on leveraging technology to modernize traditional industries.

Notable investments include Yuv, a company revolutionizing the hair salon industry with personalized hair color technology; Airship, providing software solutions for HVAC and plumbing contractors; and Reality Defender, tackling deepfake risks in cybersecurity. Ann’s approach emphasizes bridging innovative startups with legacy industries that stand to gain from technological advancements.

Beyond investing, Ann has embraced content creation, partnering with Morning Brew to develop Brew Markets. Through her media work, she highlights the interconnectedness of public and private markets, emphasizing the value of storytelling in leadership and entrepreneurship. “Storytelling is endemic in everything we touch,” Ann shared, reinforcing its importance for founders and investors alike.

Looking ahead, Ann predicts a resurgence in the IPO market by 2025 and highlights the untapped potential of AI applications, particularly in industries reliant on proprietary data. However, she cautions that overhyped AI startups must prove their scalability and real-world value.

This episode offers invaluable insights for founders and investors, from navigating leadership challenges to understanding the role of storytelling in building and scaling businesses. Tune in to hear Ann’s visionary take on the future of venture capital and entrepreneurship.

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Joe’s mission is to make investing accessible, blending entertainment with education to empower retail investors. Beyond content creation, he’s innovated by tokenizing his YouTube ad revenue, raising over $250,000 and engaging 700 investors—pioneering blockchain use in the creator economy.

In this episode of Skin in the Game VC, Joe shares insights on his journey, the future of markets, and the role of creators in finance. His story is a testament to leveraging innovation to educate, inspire, and redefine industries.

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Dave is passionate about tech innovation and values-aligned investing, favoring pre-seed to Series A stages where family offices can add real value beyond funding. His approach is hands-on and collaborative, leveraging partnerships with experienced VCs and investing in diverse tech sectors across the U.S. Family VC aims to make family offices a lasting force in the venture world, helping these investors move beyond traditional asset classes to become impactful players in early-stage tech.

Tune into this episode of Skin in the Game VC to hear more of Dave’s insights on the shifting landscape of venture capital and the role family offices are playing in supporting the next generation of innovation.

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Jeff shares how his passion for creating unique dining experiences has shaped his career, and he’s candid about the challenges along the way—whether it was opening his first restaurant with a phone tutorial from Italy or navigating the complexities of growing a business during the pandemic.

What’s really exciting is how Jeff, Tom and Saxon explore the impact of technology on the restaurant industry. From AI answering systems to cloud-based POS systems and even robotics, it's clear that tech is revolutionizing how restaurants operate. Yet, Jeff reminds us that hospitality is still about human connection, something he believes will always be central to full-service dining.

If you’re into startups, tech innovation, or just curious about what it takes to succeed as an entrepreneur, this episode is packed with insights. Plus, it’s always inspiring to hear from someone like Jeff, who not only talks about success but also how important it is to care for your investors and build lasting relationships.

This is a great listen for anyone looking to learn from someone who’s been through it all and come out stronger on the other side.

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Murphy discusses the challenges and opportunities presented by AI, emphasizing the importance of data and domain-specific expertise. He also addresses the ethical and legal implications of AI in construction, highlighting the potential for both job creation and displacement.

The conversation extends to explore the applications of 3D printing and sustainable building materials like RENCO. Murphy outlines Togalai's future goals, including global expansion and the development of new AI features.

Overall, this episode provides a valuable perspective on the future of AI in construction, its potential benefits, and the challenges that lie ahead. Tune in to hear the whole episode.

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In a rapid-fire Q&A, Zaid offers his optimistic outlook on the future, predicting AI as a job creator, Bitcoin's rise, Tesla's dominance in transportation, Miami becoming a major tech hub, and even Jake Paul's victory in his upcoming fight against Mike Tyson.

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This episode explores recent pullbacks in the crypto market – and what these changes spell out for investors – but also gets into the space-born industry and Varda, a first-of-its-kind orbital manufacturing platform, where Delian serves as co-founder. Tune in to hear Tom Wallace and Saxon Baum on Skin in the Game.

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The conversation explores Lucy's latest venture, Passes, a platform for content creators, where she emphasizes the importance of investing in engineers and discusses the role of AI in the creator economy. Lucy reflects on her move to Miami, highlighting the differences in the tech landscape and the need for increased capital in the ecosystem. Listen to find out more.

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Steve shares that the decision to move to Florence was driven by a long-standing desire to experience life abroad with his family. He reflects on the cultural differences, the historical richness of Florence, and the challenges of adapting to a different lifestyle. Steve also highlights his travels within Europe during this period.

The podcast delves into the tech scene in Italy as well a noting cultural nuances affecting entrepreneurship. In contrast to the U.S., failure is not culturally acceptable in Italy, making it a challenge for startups. Additionally, Steve provides insights into the venture capital landscape in Europe, noting the conservative approach and a lack of angel investors.

Upon returning to the U.S., Steve shares his observations on the current market environment, emphasizing the prolonged timeline for startup exits and the impact of changing economic conditions on valuations. He stresses the importance for startups to focus on profitability and cash preservation.

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Joe worked on the development of the Bootstrap app, which garnered millions of installs and revenue through a successful business model of offering free downloads of paid apps for a few days. However, the business model suffered when Apple changed the app store rules, resulting in a sudden loss of revenue.

Join Tom Wallace and Saxon Baum as Joe dives into what it looked like going from success to failure then back to success.

Link for the "State of Seed and Early Stage Investing Quarterly Update" by Saxon Baum: https://www.floridafunders.com/resources/blog/the-state-seed-early-stage-investing/

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Matthew and Michael discuss their journey of creating a car sharing app called Lula. They talk about how they came up with the idea while in college and built an app that initially had many flaws. However, over time, the app gained traction and went viral, becoming one of the top car sharing apps in the country.

They also faced challenges in securing insurance coverage for their rentals but eventually found an insurance company to work with.

The two founders emphasize their passion for insurance and how it touches every aspect of life. The two brothers mention using data points to assess risk when users sign up for their service. Michael and Matthew mention a pivotal moment in which they decided to pivot from being a car rental company to focusing on insurance. Lula provides insurance-related services, including claims management and risk reduction. They help companies save money by reducing insurance expenses and optimizing teams.

Lula has experienced significant growth, increasing their customer base from 99 to nearly 4000 companies in just over a year.

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Laura explores the robust evolution of Florida's tech industry and the state's response to COVID-19. Florida's open strategy during the pandemic made the state a magnet for tech talents, thereby catalyzing innovation. She acknowledges the pivotal role of a diverse talent pool and universities in creating a vibrant business environment.

They shift focus to Enterprise Florida, a public-private partnership established in 1996, aimed at spurring economic growth. Despite its impending merger into the Department of Commerce, Laura counters misconceptions about its effectiveness, underlining its contributions, including the Florida Opportunity Fund, its venture capital arm. She points to its successful model as proof of its integral role in Florida's economic development.

Get an inside look at emerging technologies, with Laura unveiling Florida's ambition to be at the forefront of electric vehicle take-off and landing (eVTOL) technology. Florida's geographic characteristics and existing infrastructure make it an ideal location for the deployment of this technology,

As for the current political climate, Laura expresses hope for more unity and collaboration in government. She believes challenging economic times could forge a sense of unity, leading to a more stable, effective, and trusted government.

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Join Tom Wallace as he dives into the world of angel investing in startups with Brad Feld where they’ll discuss his successes, what it takes, and where startup investing could be going.

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If you want to learn more about investing in early-stage tech like a venture capitalist, be sure to visit the Florida Funders website at floridafunders.com. Join our angel network at no cost and get access to Florida Funders VC-vetted investment opportunities in the next great breakout tech companies. 

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If you like what you hear, please rate us 5 stars and check out other episodes here: https://www.floridafunders.com/category/podcast/

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If you like what you hear, please rate us 5 stars and check out our site: https://www.floridafunders.com/category/podcast/

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For Elias Torres, the choice his mother made when she immigrated from Nicaragua to Tampa would prove to be a fortuitous one in helping him realize that dream. After his early start at IBM, Torres became committed to the vision of entrepreneurship. With Drift, his current company, he has proven time and again that Latino founders deserve a place amongst the world’s biggest capital projects. 

Torres is the founder and CTO of Drift, the world's leading conversational marketing and sales platform. Drift helps businesses connect with customers who are ready to buy. After just three years in the market, Drift has become one of the fastest growing SaaS companies of all-time and was named to the Forbes Cloud 100, LinkedIn Top 50 Startups, Entrepreneur's Top Company Cultures, Boston Business Journal's Best Places to Work, and SaaS Company of the Year by the NEVCA.  

Listen to today’s episode of Investing in Florida Technology and hear how Elias made the incredible leap from struggling to take orders in English at his fast food job as a teen to becoming Chief Technology Officer of his own company. He also discusses dealing with imposter syndrome, starting with a new company just weeks before the 2008 crash, and the major expansion plans he has for Drift.

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Some Questions Asked: 

• You came here at a young age from another country, can you tell us about that? (01:37)
• What was your first entrepreneurial venture? (12:32)
• Can you tell us about Drift, your current company? (17:30)
• Can you explain to the listeners the difference between venture capital and private equity? (31:29)
• Would you ever consider moving Drift’s headquarters to Florida? (39:59)

In this episode, you will learn:

• How and when Torres became interested in tech (03:48)
• Torres’s early start with IBM (06:42)
• What the original vision was for Drift (21:43)
• Why venture capitalists love first generation immigrants (25:49)

Connect with Elias:

• LinkedIn
• Website
• Drift

Hosted on Acast. See acast.com/privacy for more information.

For venture capitalist David Blumberg, the pandemic took him from his ancestral home of California across the country to Florida. Realizing that he was no longer chained to his fixed, physical office in San Francisco, he took the plunge and moved over 3,000 miles in order to take advantage of the up-and-coming vibe of Miami, as well as the state’s business-friendly regulations and taxes. David learned how to take advantage of the pandemic and was able to recognize it as -- as he puts it -- a catalyst of virtualization, innovation, and decentralization.

Blumberg is the founder and managing partner of Blumberg Capital, a  private Venture Capital firm investing in early-stage IT, digital media, social media, mobility, Internet, e-commerce, payments, SaaS, and tech-enabled services. He also serves as a board member of Credorax, Trulioo, IntSights, and Slync.io. David holds an undergraduate degree from Harvard University and an MBA from Stanford University Graduate School of Business.  

Listen to today’s episode of Investing in Florida Technology and find out how David made the leap from studying government to becoming a venture capitalist, how he embraces virtualization, and why he believes that the 21st century will be one of massive innovation and productivity for office and service work. 

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Some Questions Asked: 

• Can you tell our audience a bit about your background and where you grew up? (01:54)
• You have this tie with Israel, when did that start? (14:10)
• What do you see in Florida and Miami? (22:41)
• What are you looking for in a founder? (29:38)

In this episode, you will learn:

• Why Miami made the top of David’s list when he and his family decided to relocate (03:16)
• About taking ‘acorns’ and turning them into unicorns (09:41)
• How patience has paid off for Blumberg Capital (12:57)
• A little about the Israeli company that David and Tom are both investors in (20:01)
• Venture capitalists either follow the NASCAR model or the marionette model (33:59)

Connect with David:

• LinkedIn
• Blumberg Capital
• Twitter

Hosted on Acast. See acast.com/privacy for more information.

Brian Murphy founded ReliaQuest in 2007, just as the US was plunging into the Great Recession. While he didn’t know it yet, a DoD contract would come to be instrumental in the company’s pivot from IT to cybersecurity. In the years following, Murphy was able again to lead the company with flexibility to a market that better suited them. 

Murphy is the CEO and founder of ReliaQuest, a cybersecurity company serving enterprises globally. ReliaQuest, the leader in Open XDR-as-a-Service, is known for being the force multiplier for security operations teams. He also serves on the board of Embarc Collective, a Tampa Bay-area startup incubator, and is an official member of the Forbes Technology Council. 

On today’s episode of Investing in Florida Technology, Murphy speaks about the evolution of ReliaQuest, his advice to founders that are just starting out, and how he still finds time to serve as a chairman on the board of Embarc Collective. He also discusses the big pivot that brought ReliaQuest to where it is today and what he sees happening in the industry looking ahead. 

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Some Questions Asked: 

• Can you tell us a little about your background? (01:50)
• How did you make the switch to recurring revenue? (06:20)
• Have you had any trouble attracting talent in Florida? (08:47)
• How did COVID affect ReliaQuest? (12:02)
• Where is most of your hiring taking place? (14:06)
• Are you being acquisitive? Or are you still just growing organically? (15:58)

In this episode, you will learn:

• What inspired Murphy to start ReliaQuest (2:41)
• A little about the software team at ReliaQuest (07:50)
• About the growing cybersecurity industry in Tampa (10:57)
• Brian's experience with bootstrapping (14:53)
• Where Brian sees ReliaQuest going in the next 5-10 years (23:04)

Connect with Brian:

• LinkedIn
• Reliaquest

Hosted on Acast. See acast.com/privacy for more information.

When Campbell entered West Point fresh out of high school, he never dreamed of the opportunities that would soon be accessible to him. Through his work as a communications officer, Campbell learned invaluable lessons about leadership, problem-solving, and tech. After leaving the military and joining the private sector, Campbell put to work the skills that he had honed, which led directly to his many successes and a career as an “accidental entrepreneur.” 

Campbell currently serves as President of AC4S Technologies, a hybrid cloud solutions provider. Prior to his current position, he served as CEO of AC4S for 16 years. Before that, he held positions in planning, designing, and implementing large-scale telecommunications networks for companies like Intermedia Communications and Accelacom. He also serves as Chairman of the Board for the CEO Council of Tampa Bay and as a member of the board of trustees for BayCare Health System. 

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Some Questions Asked: 

• Where did you grow up and how did you end up at West Point? (04:07)
• Where did you go after you left the military? (07:10)
• How did West Point and the military prepare you for being an entrepreneur? (11:21)
• How can people like me invest more in minority founders? (18:25)

In this episode, you will learn:

• About AC4S Technologies and where the name came from. (02:25)
• How Campbell became what he calls an “accidental entrepreneur.” (08:21)
• The advice Campbell has for young, hungry founders who are just starting out and why it’s so important to make sure you’re really vetting the partners you’re going into business with. (12:34)
• Why being an entrepreneur isn’t for the faint of heart and easily discouraged—and why it’s best to play the game as a team sport. (15:22)

Connect with Hugh:

• LinkedIn
• AC4S Technologies

Hosted on Acast. See acast.com/privacy for more information.

Arnie Bellini began his career at Price Waterhouse just as personal computers began their evolution from space-age technology to household necessity. Realizing the potential of this type of tech, he quit his consulting job, founded a company to help small businesses optimize their servers, and never looked back. 

Bellini is co-founder and former CEO of ConnectWise, a provider of IT services to companies in the Tampa market and the publisher of the industry's most widely-used business operating system.  He currently serves as managing partner of Bellini Capital, an investment firm based in the Tampa area. 

Listen to today’s episode of Investing in Florida Technology and learn Bellini’s start-up origin story at the dawn of the PC, why he believes it’s so important to balance your work life with family and hobbies, and how he equates the lessons he gained training to swim the English Channel to his business philosophy. 

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Some Questions Asked: 

• What was the dynamic like between you and your brother when you started your company as business partners? (03:32)
• When you started, did you envision that you would be building a company that you would sell for over a billion dollars? (04:24)
• When was the tipping point when you realized that you had become more of a software company? (11:08)
• How is your family involved in Bellini Capital? (16:18)
• What advice would you have for founders out there? (20:13)
• What kind of investments and things are you looking for that excite you? (24:32)

In this episode, you will learn:

• A bit about Bellini and his experience as a founder of ConnectWise. (02:09)
• How Bellini became a programmer—out of necessity. (08:24)
• About Bellini’s experience becoming one of the few people over 50 to swim the English Channel. (12:52)
• How Bellini Capital is working to help preserve the Florida Wildlife Corridor. (16:56)
• The importance of work/life balance in order to avoid burnout as an entrepreneur. (21:52)
• What Bellini finds most exciting in the world of up-and-coming technology. (27:41)

Connect with Arnie:

• LinkedIn
• Connectwise

Hosted on Acast. See acast.com/privacy for more information.

Reuben Pressman started on the journey that brought him to where he is today when he began coding as a 10-year-old. As a student at the University of South Florida, he realized that the majority of the learning he was doing was going on outside the classroom—and that student involvement was a huge blind spot at his and many other schools.  

After this a-ha moment as a student, Pressman set out to make it easy to collect usable data, then give the tools that institutions needed to make an impact. Launched in May of 2014, his company Presence has spent the last seven years doing just that.  

Pressman is the founder and has served as CEO of Presence for more than nine years. The software serves to help universities improve retention rates by tracking data related to student involvement patterns and behaviors. In addition, he was recently announced as the CPO at Modern Campus, a higher education software company. He also serves as Entrepreneur in Residence for the city of St Petersburg, Florida.

Find out why Pressman believes the most important trait in an employee is their ability to be a team player and the fortuitous way he first connected with Tom, in today’s episode of Investing in Florida Technology. 

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Some Questions Asked: 

• What can you tell us about Presence and the journey that brought you here? (03:08)
• Who was your first customer? (05:17)
• Where was the tipping point when you realized you would be able to scale and grow the company? (08:20)
• Tell us about your time as the Entrepreneur in Residence for the city of St Pete. (12:50)
• What made you decide that it might be time to sell? (17:54)

In this episode, you will learn:

• How Presence and its mission grew out of Pressman’s observations about his own college experience. (03:20)
• How Pressman worked through all of the bureaucracy involved in selling to universities. (06:42)
• The fundraising journey behind Presence. (09:45)
• Pressman’s advice for founders who are just starting out right now. (14:47)
• Where Pressman sees himself going after Presence. (21:02)

Connect with Reuben:

• LinkedIn
• Presence
• Twitter

Hosted on Acast. See acast.com/privacy for more information.

After emigrating to Miami as a young teen and—as he puts it—surviving high school, Medina was able to develop a unique and valuable perspective on the US-Latin American market. From his jetsetting early years as a CPA at PricewaterhouseCoopers, to his time in Kuwait helping rebuild after the liberation, to creating network access points while the internet was still in its infancy, Medina has frequently been at the center of some of the most important industry events of the last 50 years. 

Medina’s decision in the late 1980s to take the leap of faith from real estate to tech when he found himself at a crossroads might’ve been the most important move he ever made. He was able to reinvent himself and his company, Terremark, once again, from a highly successful developer to an early adopter of burgeoning internet tech, where he found his true calling.

Medina served as Chairman of the Board, President, and Chief Executive Officer of Terremark until 2011, when the company was acquired by Verizon Communications. In 2012, he founded Medina Capital, a private equity firm with a focus on emerging cybersecurity technologies where he currently serves as managing partner. He is also the founder and chairman of eMerge Americas, a tech networking event that serves to connect the US, Latin America, and Europe.  

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Some Questions Asked: 

• What made you decide to take the risk of leaving your job at Pricewaterhouse to become an entrepreneur? (05:13)
• How long did you have your first firm? (7:23)
• What was the turning point where you realized your company would survive the dot com bubble bursting? (14:49)
• How much change has there been since you started in the ability to recruit for tech positions within Florida? (20:31)
• What's Medina capital working on now? (23:21)

In this episode, you will learn:

• About Medina’s experience immigrating to the US from Cuba at 13. (02:25)
• How the real estate crash of the late ’80s spurred Medina’s move to tech. (08:07)
• The origin story of Terremark Worldwide. (09:51)
• The one surprising thing Medina did after Terremark was sold that he had never allowed himself to do before. (16:28)
• Where Medina sees Miami’s tech industry going in the next 5-10 years. (26:26)

Connect with Manny:

• in the Miami Herald
• on Wikipedia
• Medina Capital

Hosted on Acast. See acast.com/privacy for more information.

Claudia works with Endeavor Miami, a global organization in over 30 markets, to identify high-impact entrepreneurs—those who have big ideas and are taking their ideas to the next step. Endeavor then works with those entrepreneurs to accelerate their growth by creating connections with mentors and investors.  

We talk about what Endeavor is doing to encourage and stimulate start-ups, and Claudia takes me through her personal history, from her roots in El Salvador to her time as a finance major at Penn State. Claudia also tells me what it takes for a company to be selected by Endeavor, what their mentorship program looks like, and how once you’re an Endeavor entrepreneur, you’re part of that global network for life. 

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Some Questions Asked: 

• Can you tell us a little about Endeavor Miami’s mission?  (02:47)
• How did you get from El Salvador to the United States? (04:46)
• What are you looking for in these companies you choose to take into a cohort? And what does that process look like? (07:21)
• How many companies will apply for you to get to your 10? And what are you looking for in those 10 companies that you end up choosing? (12:02) 
• How many companies have you seen go through your program since you’ve been in Miami? 
• Are there any portfolio companies you want to highlight? That you're very excited about? (20:42)

In this episode, you will learn:

• A bit about Claudia’s personal background (03:51)
• What the cohort experience looks like for companies that are selected by Endeavor (09:41)
• How some companies end up pivoting their business model as a result of their time with Endeavor (13:44)
• What happens with the entrepreneurs after Endeavor’s mentorship is over (16:54)
• Why Florida is the site of the next big tech ecosystem (26:54)

Connect with Claudia:

• LinkedIn
• Endeavor

Hosted on Acast. See acast.com/privacy for more information.

Join me today as I welcome Rennick Palley, founder and CIO at Stratos Technologies. Rennick is an MIT graduate who started his career on Wall Street before turning his interest toward financial technology. He is also a co-founder of Goldfinch Finance, a decentralized global bank that aims to change the face of investing in businesses. 

We unravel the differences between Bitcoin and Ethereum, the relevancy of blockchain supply and demand, and how we may be looking at a not-so-distant future in which only a few of these new currencies remain relevant. Rennick also expands on the implications of blockchain in regards to global finance, and what that could mean for business finance over the world.

Find out how Rennick went from Wall Street to venture capital projects, and how the professional mentoring he gained at a global equity fund helped him get there. Learn why Rennick believes that productivity is driven by technological advances, his view on the pitfalls of consumer banking in the US, and what led him to the world of blockchain and crypto. 

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Some Questions Asked: 

• How did you end up at MIT? (4:08)
• What took you from Wall Street to the world of crypto? (5:56)
• How would you compare Bitcoin to Ethereum? (10:09)
• Do you think that we’ll eventually only have a few different cryptocurrencies? (14:06)
• What is China’s place in all of this? (25:14)
• What can you tell us about Goldfinch Finance? (29:09)

In this episode, you will learn:

• A bit about Rennick’s professional background (2:14)
• How Rennick’s beliefs about investment strategy changed over time (4:44)
• About Rennick’s professional mentor (6:01)
• The difference between crypto, DeFi, and blockchain (16:20)
• The implications of a liquid form of currency on the global economy (25:13)
• The key differences between angel investing and the Goldfinch blockchain system (33:33)

Connect with Rennick:

• Stratos Technologies
• email
• LinkedIn
• Twitter

Hosted on Acast. See acast.com/privacy for more information.

If you’ve ever found yourself at a crossroads in your career and felt that you just aren’t being offered anything to your liking, have you ever thought of striking out on your own? Entrepreneurship is a complicated and humbling experience, but it also allows you to be your own boss and create the business you’ve always wanted to work for. 

What happens when a former Army officer and member of the White House Homeland Security board retires from the military and decides to make his own luck? You get Brian Butler, founder and CEO of Vistra Communications. From college ROTC to working at the Pentagon to founding his own startup, Brain has experienced firsthand a remarkable professional career. 

Vistra Communications handles PR, marketing, and consulting for a number of government and corporate contracts, including AT&T and Coca-Cola. Founded in 2007, they now employ over 100 people and have offices in both Florida and Northern Virginia. 

As a 22 year veteran of the US Army, Brian has learned invaluable lessons through his service. Listen and learn what Brian attributes his success to and what we can do to help diversify the growing field of Florida entrepreneurs. 

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Some Questions Asked: 

• How did you transition from the army to entrepreneurship? (4:33)
• How did the military prepare you for the rollercoaster of business ownership? (7:22)
• What did the army teach you about leadership? (8:50)
• How can we fix the disparity in diversity amongst entrepreneurs? (14:58)
• What impact does technology have on your business? (19:16)
• Where does the military stand on adopting and developing technology? (21:22)

In this episode, you will learn:

• How Brian got started as an entrepreneur. (2:27)
• Why Brian believes that veterans make excellent employees. (6:05)
• The type of attitude that makes a successful business leader. (11:15)
• About the emerging start-up scene out of South Florida. (18:24)
• Advice Brian has for founders. (25:13)

Connect with Brian:

• LinkedIn
• Vistra Communications
• Vistra on Facebook
• Vistra on Instagram

Hosted on Acast. See acast.com/privacy for more information.

If you’re serious about making it in the tech world, there are certain attributes that will set you apart from the pack. Curiosity, humility, and the ability to see patterns are invaluable for anyone, but are absolute prerequisites for successful entrepreneurs. Couple these with a shrewd eye for team building and a knack for playing to your own strengths, and you may be well on your way to success. 

When you hear names like Bill Gates and Mark Zuckerberg, the first thing that comes to mind will, of course, be that they’re titans in the tech industry. What might not immediately strike you is that they both built their empires from the ground up. Steve Raymund is one of the few others who also own that claim to fame. From his beginnings at the dawn of the 1980s tech boom to his diverse stable of investments today, Steve has managed to remain at the top of his game throughout the last 40 years. 

Steve Raymund is the former CEO, co-founder, and board member of Tech Data, an IT products and services company headquartered in Clearwater, Florida. Steve led the company through early turmoil and self-described “rock bottom” during a nearly complete employee turnover, to going public a mere six years later, with $1 billion in annual sales by 1993. 

Steve also serves as a board member for Jabil Inc, a $19 billion technology manufacturing company that provides parts to Apple and Microsoft. 

As a 20-year CEO, Steve has learned some invaluable lessons. Find out why Paul touts Steve as a different kind of tech executive and the traits and personality type that Steve attributes much of his success to. 

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Some Questions Asked: 

• To what do you attribute Tech Data’s longevity?  (12:57)
• What have you learned about managing people and creating a team? (17:30)
• Is there one accomplishment in your career that stands out, that you're most proud of? (19:29)

In this episode, you will learn:

• Steve’s experience as an early player in tech. (00:56)
• What the rapidly growing tech marketplace, starting in the early '80s, looked like. (02:26)
• The unique qualities that make up a different kind of tech leader. (7:11)
• What to really look for in an angel investment opportunity. (25:48)
• The key to making it all look so easy (and why the pain along the way is worth it!) (30:09)

Connect with Steve:

• LinkedIn

Hosted on Acast. See acast.com/privacy for more information.

In this episode, Tom Wallace talks in detail about these five important elements that every investor should pay attention to and rigorously follow whenever the opportunity to invest comes their way.

Tune in, and learn more about the 5 Ds of Angel Investing, and how Florida Funders can help both investors and founders to reach higher grounds in their ventures.

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In this episode, you will learn:

• The 5 Ds of Angel Investing and why they are crucial for a successful angel investor. (00:45)
• The importance of being selective about the companies you’re investing in (01:45)
• The two parts of the due diligence process required for a great investment. (02:46)
• The role played by domain expertise in having successful investments. (08:32)
• The reason we encourage our investors to build a diversified portfolio. (09:52)
• Why discipline plays a crucial part in angel investing. (11:14)
• Why Florida Funders is making angel investing easy. (12:46)

Connect with Tom Wallace:

• LinkedIn
• Florida Funders website

Hosted on Acast. See acast.com/privacy for more information.

After interviewing a handful of people on the show and finding out what makes them tick, what motivates them, how they’ve built successful companies, and how they help others do the same, we thought it’s time to give you some background on Florida Funders – what sparked the idea and why it’s a great network for founders and funders.

Our host and Managing Partner, Tom Wallace, shares his journey in the angel investing world, as well as what drove him and his partners to start Florida Funders. Tom has learned the hard way how challenging angel and early-stage investing can be, and he has dedicated his life to making this process easier.

Tune in to learn more!

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In this episode, you will learn:

• What brought Tom to Florida almost 30 years ago. (00:45)
• The current Florida tech ecosystem. (02:28)
• The venture that inspired Tom to dedicate full-time to angel investing. (04:01)
• What Florida Funders offers to investors. (08:15)
• The benefits of Florida Funders’ angel network. (09:58)

Connect with Tom and Florida Funders: 

• Florida Funders website
• LinkedIn

Hosted on Acast. See acast.com/privacy for more information.

In today's episode, Ashley Jarocki and Stephanie Markese share with us how they went from cheering on the same line together to making a leap of faith and starting their own company in the staffing world. 

Stephanie Markese always wanted to be a dentist until she realized that she wanted something more than work for a salary for the rest or her life, where she could evolve and make her earnings grow. After a taste of staffing and sales, there was no coming back into dentistry. 

Ashley Jarocki was looking for a change after five years in the corporate world. One day, she received a call from Stephanie proposing a leap of faith: bring your knowledge of the corporate world and let's start a company together. 

Listen to the full episode, learn about the best way of dealing with the hiring process, how our guests think the staffing world will look like in the coming years, and how AI will deal with culture fit when filtering candidates for hire. 

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Questions I ask:

• Did you guys go into staffing together? (4:11)
• Your industry changed a lot in the last year. How did COVID affect your business? (7:30 )
• Any advice for entrepreneurs buildings their team? Should they do it themselves or hire a staffing firm? (10:13)
• Is it possible to evaluate a candidate in a one-hour interview? (14:28)
• How do you see things like 5G, AI, augmented reality, and other new technologies affecting your industry? (17:51) 

In this episode, you will learn:

• How Next Path was born (4:18)
• Recruiting and staffing evolving with technology (7:30)
• The reason why companies should look for culture fit when hiring (11:06)
• AI or a person, who is better for culture fit? (20:56)
• Are resumes still relevant in the LinkedIn era? (22:29)

Connect with Ashley Jarocki:

Linkedin

Instagram

Facebook

Connect with Stephanie Markese:

Linkedin

Instagram

Facebook

Next Path Resources:

Website 

Linkedin

Facebook

Twitter

Instagram

Hosted on Acast. See acast.com/privacy for more information.

As an investor, you have to be a calculated risk-taker. Of course, there’s the due diligence that can help you decide whether the business that’s presented to you is worth funding, but you still need a dose of courage to financially support an idea 

Netflix is one of those successful businesses that weren’t short of ups and downs – and in this episode, you will hear the story of Netflix seen through the lens of one of the early investors: Paul Holland. Why did he choose to invest? What’s the background between Paul and Reed Hastings? And how did Netflix become one of the clear winners of the streaming wars? Tom and Paul also discuss the important role Paul’s new firm, Mach49 plays in helping global businesses drive meaningful growth to beat the startups at their own game.

Paul Holland is Managing Director and VC-in-Residence at Mach49, where he leads the company’s Corporate Venture Investing Practice. Paul works with global businesses to design, launch, and manage corporate venture funds that leverage the experience, deal flow, global network, and success of his top-tier Silicon Valley VCs.

Prior to joining Mach49, he was a General Partner for 18 years at leading venture capital fund Foundation Capital, helping take startup companies from zero to $100M, to IPO, or acquisition. His amazing background also includes partnering with Reed Hastings at Pure Software and joining Mark Gainey at Kana Communications.

Paul enjoys being on the front lines, working side by side with entrepreneurs developing fast-growing, dynamic new ventures. His investing stories are diverse and interesting, so tune in and find out how he met Reed Hastings and invested in Netflix, how he supported Chegg, as well as what Mach49 is all about.

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Some questions asked:

• How did the investing in Netflix come about? (02:47)
• When did you realize Netflix is really something special? (14:17)
• What do you look for in founders? (18:03)

In this episode, you will learn:

• Paul’s journey to where he is today. (00:54)
• The landscape of venture capital in the late ‘90s. (06:02)
• The challenges faced by Netflix in its early beginnings. (08:36)
• How Chegg became a decacorn. (20:23)
• Linda Yates’ journey to founding Mach49. (24:41)
• The five preconditions for success. (27:04)
• The reason more and more people are migrating away from Silicon Valley. (30:33)

Connect with Paul:

• LinkedIn
• Mach49 Website

Resources:

• Something Ventured – the movie

Hosted on Acast. See acast.com/privacy for more information.

Adam Struck is a Floridian but he is currently living in LA with his family. Through his company, Struck Capital, he supports young founders providing core technology innovation to tackle the world’s largest problems. Adam and his team of investors focus on seed investments into companies led by visionary technologists.

Adam is a very successful young man who was named the Forbes 30 Under 30 Most Influential People – and in today’s episode, he is going to share his journey from being a lawyer to dedicating himself to transform LA into a place known for technology. We dive deep into his mindset and Struck Capital’s mission, as well as some successful deals he’s had over the years.

Tune in, to learn more about the changing landscape of LA and the investment opportunities you can find there.

Some Questions I Ask:

• After you left the law firm, did you go right on to start your own firm? (03:57)
• Tell us more about the journey at Struck Capital. What was your vision from the beginning? (07:31)
• How did you get to move to LA? (08:42)
• What is the main way you’re able to help founders grow their business? (15:08)
• How did you find out about the Postmates deal? Are you still in it today? (17:35)
• Have there been any investments that you passed on that you look back on and they really took off? (19:43)
• What stage are you typically investing in? (21:46)
• What do you see as the innovation and the opportunities in your area that you tend to look at? (25:00)

In This Episode, You Will Learn:

• Adam’s journey from lawyer to being a venture capitalist. (01:20)
• The entrepreneurial history of Adam’s family. (02:54)
• The advantages of doing SPVs – Special Purpose Vehicle. (10:12)
• The landscape in LA, in terms of tech companies. (11:07)
• The reason Struck Capital was able to capture a lot of market share in a short time. (12:39)
• The typical Struck Capital cheque size for investments. (22:28)
• The partnership between Adam’s company and Leonardo DiCaprio’s platform. (23:33)
• Adam’s advice for investors. (27:00)

Connect with Adam Struck:

• Struck Capital Website
• LinkedIn

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As an entrepreneur turned successful angel investor himself, Jason knows how to spot a product that was crafted for growth. He’s had a front row seat to the way that both startup investing and working for startups is evolving in light of Covid. 

 exactly what he needs from his founders - and keeping him in the loop with regard to the health of your business is crucial. In today’s episode, he discusses why he’s eyeing a potential move outside of Silicon Valley, what it takes to make a truly remarkable product, why angel investors should ask for a board seat – contrary to what many people believe – and what types of companies to avoid if you’re just starting your investing journey.

Jason knows his game, so check out this episode to learn more about his thoughts on what’s happening with the current investment landscape, how to keep your investments close, and finding startups that are worth your investment. 

Some questions I ask:

• How did you get started in angel investing, and what were you doing prior? (06:05)
• What’s the one thing you look for in founders? (12:26)
• At which stage do you like to invest? (14:04)
• How many boards do you sit on? (23:23)
• What do you think the future of crowdfunding is? (30:03)
• If you look at the game-changing technology that’s coming on board these days, are there certain ones that you are most excited about? (41:45)

In this episode, you will learn:         

• The changes the pandemic has brought in terms of doing business and closing deals. (02:27)
• The story of Uber – what it was originally and how Jason ended up investing in it. (08:13)
• How Airbnb was a unicorn that most people thought it was a bad idea. (10:46)
• The types of companies you should avoid investing in if you’re a new angel investor. (14:36)
• Jason’s four-bet strategy when he’s investing in a company. (16:18)
• The importance of monthly monitoring your portfolio of investments. (18:30)
• The two things Jason requires founders in their term sheets: to receive monthly updates and to have the option of a board seat. (21:34)
• How regular board meetings can help founders when they’re discussing with investors. (22:10)
• The global trend around risk and the importance of investing no more than 20% of your income average in startups. (31:50)
• The advantage of collaborating with an Angel Group. (40:13)
• Jason’s advice for people who want to venture into the podcasting world. (45:06)

Connect with Jason

• LinkedIn
• Email: jason@calacanis.com
• Angel University
• This Week in Startups Podcast
• Book: Jason Calacanis – Angel: How to Invest In Technology Startups – Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000

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That’s exactly what our guest today focuses on – finding people that he knows he could trust and that are willing to go the extra mile for their business. Jeff Vinik is a man wearing many hats and throughout his professional career, he’s managed to switch from being a successful Wall Street investor to then being a hedge fund guy, to joining the real estate industry, to owning a sports team – the Tampa Bay Lightning – and on top of that, to being an early-stage tech investor.

Being in Jeff’s shoes is not an easy ride, and it takes a certain discipline in doing your due diligence and learning as much as you can about the industry you’re in or you’re thinking of joining. Today, we discuss his professional journey, why he wanted to switch gears and be part of multiple areas, as well as the types of people that he aims at surrounding himself with.

If you’re curious to learn more about Jeff and his early-stage investing, then tune in, and enjoy the show!

Some questions I ask:

• How did you go from hedge fund to real estate? (02:19)
• How has COVID affected your business? (07:42)
• How did you get into early-stage technology investing? (12:20)
• Do you have any stories there about a deal that you invested in that you’d never do again? (16:34)
• What do you look for in founders? (17:44)
• What do you do in your spare time? (29:38)

In this episode, you will learn:

• The role Bill Gates plays in Jeff’s real estate ventures. (06:35)
•  Jeff’s thoughts on how the Tampa Bay area is going to evolve post-COVID. (04:40)
• The four Ds of angel investing. (15:29)
• Jeff’s experience with investing in eSports. (21:11)
• The story of Embarc Collective. (24:37)

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Throughout this episode, Ryan shares how he bucked the trend, refusing to undergo extreme financial stress like many other retired athletes. Instead, he treats business like a team sport, acknowledging that he’s only as good as those he surrounds himself with. Ryan breaks down what motivates him to pursue venture capital, how he evaluates the founders whom he invests in, and how he believes more founders from minority communities can get the funding they need to scale. 

Some Questions I Ask: 

• How did you buck the trend of becoming financially stable after retiring from the NFL? (6:45)
• What did your role look like with StraightCast Media? (14:40)
• What do you look for in founders? (24:02)

In This Episode, You Will Learn: 

• How Ryan’s career led him to venture capital. (2:11)
• What inspired Ryan to co-found his business StraightCast Media. (10:08)
• Why Ryan decided to directly invest in Peloton early on. (21:05)
• How Ryan evaluates the founders he wants to work with. (27:20)
• How education and exposure will help founders from minority communities get the funding they need. (31:52)

Connect with Ryan Nece: 

LinkedIn

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In this episode, David shares his journey to becoming a successful investor over the last 6 years, including his biggest mistakes and success stories. Furthermore, he discusses how the global COVID-19 pandemic affects his current investments, and what he believes the “new normal” will be like after the pandemic. 

So get ready to hear more about David’s success story and learn about new and unique investment opportunities in the market now. 

Some Questions I Ask: 

• What kind of investing do you do? (2:49)
• What do you look for in a founder? (6:03)
• What’s your big miss? (14:39)
• What opportunities do you see presenting themselves as we transition into this “new normal”? (16:57)
• What investment are you most excited about? (22:43)
• What advice do you have for other investors? (25:48)

In This Episode, You Will Learn: 

• How David got to where he is today. (1:19)
• David’s strategy for investing in technology: focus on companies reshaping the world. (2:56)
• The process of David’s decision to invest in a deal with an outdoor gear rental company. (6:59)
• How the COVID-19 pandemic affects investments. (10:38)
• Why pet food companies are great investment opportunities. (15:26)
• What the future of valuations looks like. (20:50)
• What drew David to his first investment. (24:13)

More about Florida Funders: 

Website

Our Investment Process 

LinkedIn

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In this episode, Peter shares insights into how he became an investor, how he handles his clients’ wealth, what role the timing of markets plays in his strategy. He also shares some knowledge from his book, The Five Mistakes Every Investor Makes, including what big behavioral mistakes investors should avoid. 

So get ready to see investing in a new light and discover strategies to grow your wealth. 

Some Questions I Ask: 

• Tell us about your background and your firm. (1:40)
• What drew you to the world of investing? (3:22)
• What’s your approach to investing and growing your clients’ wealth? (4:30)
• How do you look at the timing of markets? (11:21)
• When you look at the dry powder from private equity, what does that mean for investors going forward? (26:00)

In This Episode, You Will Learn: 

• How Peter transitioned from an advisor to investor. (3:26)
• How Peter customizes investment plans for his clients. (4:40)
• What big behavioral mistakes investors tend to make. (6:24)
• Why Peter avoids getting involved in venture capital. (16:28)
• Why people choose private equity investments over public markets. (26:28)

Resources: 

The Five Mistakes Every Investor Makes by Peter Mallouk

Creative Planning

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In this episode, Chris shares his story and every step he took to find the success he has today. He goes further to share advice for other founders, how his vision for business shifted to focusing on angel investing, and how he became Entrepreneur of the Year. 

So get ready to learn Chris’s success story and how he sees the future of the restaurant business. 

Some Questions I Ask: 

• How did Outback Steakhouse come about? How did you get started? (0:56)
• Where did the Australian theme for your restaurant come from? (5:28)
• What did you learn throughout your journey that other founders should know? (10:03)
• When did you start angel investing? (15:46)
• When looking at angel investing, how much emphasis do you put on a jockey? (24:53)
• From a technology standpoint, what do you think is the biggest impact we’re going to see in the restaurant industry in the next 5 years? (29:42)

In This Episode, You Will Learn: 

• How Chris’s vision for his business continuously developed over time. (7:36)
• What makes business a team sport. (10:14)
• How Chris was awarded Entrepreneur of the Year. (11:55)
• How delivery technology is changing the restaurant experience. (27:43)

More about Florida Funders: 

Website

Our Investment Process 

LinkedIn

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In this episode, Scott shares some of the insights and lessons he learned as part of the team at Uber, and what his transition to angel investing was like. He explains a few of his top lessons learned from his investment experiences so far, including why he enjoys working with founders in groundbreaking situations. 

So get ready to learn about what the future of investing in technology looks like. 

Some Questions I Ask: 

• What lessons did you learn at Uber? (3:38)
• How did you get started in angel investing? (8:52)
• How do you get involved with the companies you invest in? (10:36)
• What area of technology are you focusing on? (18:43)

In This Episode, You Will Learn: 

• What the evolution of Uber looked like. (3:06)
• Why Uber’s IPO is changing drastically & what to expect in the future. (7:19)
• What Scott’s learned from angel investing. (9:02)
• How valuations differ outside of Florida. (12:35)
• Why Scott enjoys working directly with founders. (16:43)

More about Florida Funders: 

Website

Our Investment Process 

LinkedIn

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Oftentimes you trust your gut when deciding to put your finances, effort, and time into a company. In the early stages, you partner up with friends and family, and you choose your investments based on whether you like those people or not. But, as you move further down the spectrum, it becomes more science.

In today’s episode, Steve and I discuss how to choose the companies you want to financially support, and also, some of the red flags for angel investing.  

Steven MacDonald is a serial entrepreneur who founded, among others, TechHealth and myMatrixx – the first web-enabled pharmacy benefits manager. The successful experiences in the entrepreneurial world led Steve into angel investing and now he is a Partner and a Board Member at Florida Funders and he helps find, fund, and build the next generation of technology companies in Florida.

So, listen to Episode 06, to learn, from an expert in the field, what are the rewards of angel investing and how you can actively be involved in the companies you want to support.

Questions I ask:

• While you were building myMatrixx, what were some of the things that you learned, lessons learned as an entrepreneur, that maybe even help you as an angel investor today? (04:00)
• When and how did you start angel investing? (05:31)
• What do you look for in a founder? What is it that excites you? And why you want to invest in this founder and not that founder? And is the founder the most important thing? (11:38)
• What are some of the things that you, as a board member and investor, can help a company with? (17:05)
• What differences do you see between the startup community and investing in Silicon Valley, San Francisco versus Florida? (20:45)

In this episode, you will learn:

• Steve’s background in the business world. (01:54)
• The reasons angel investing is viewed as part art, part science. (06:03)
• What to look for, when considering to invest in a company. (10:27)
• Our processing power and Moore’s law – the two essential components that spin the wheel of technology advancement. (14:46)
• Steve’s favorite companies that he has invested in. (20:00)

Connect with Steve:

• LinkedIn

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On today’s episode, I am joined by Alexis - one of the co-founders of Reddit, who is an important player in the angel investing area, and Andrew – the founder of Papa, a Florida-based company. Alexis invested in Andrew’s business, and they are sharing with us their entrepreneurial journey.

Alexis Ohanian co-founded Initialized Capital with Garry Tan, in 2012. Alexis's expertise includes product, marketing, and community, and he is a prolific early-stage investor. Alexis was a co-founder of Reddit, the third-largest website in the US, which was funded by Y Combinator in 2005 and acquired by Condé Nast in 2006. He also served as a partner at Y Combinator and wrote the bestselling book Without Their Permission.

Andrew Parker is the founder and CEO of Papa – a Florida-based tech startup. He started the company to support a personal need with his grandfather. Papa provides on-demand personal assistance and socialization to seniors.

So, listen to Episode 05, to learn about the future of Florida, tech-wise, and what we can do to attract more people to start their business here.

Questions I ask:

• How did you guys meet? (07:51)
• Andrew, I saw you expanded geographically. Tell us about that. (11:52)
• Alexis, what do you think of the deal flow here in investments versus California? (12:39)
• What tech do you see coming down the road, in terms of technology, from an investment standpoint? (16:33)
• Have you had any issues with recruiting people you need? (20:43)

In this episode, you will learn:

• How Initialized was born. (02:32)
• How Papa became a business. (04:21)
• Alexis’s experience with Y Combinator. (05:26)
• The reasons why technology can never replace the human touch. (18:08)
• What Florida needs to do right now, to become an important player in the tech space. (21:22)

Connect with Alexis:

• Initialized Website
• LinkedIn

Connect with Andrew:

• Papa Website
• LinkedIn

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Stuart is a native of Tampa, Florida. He moved around, went to school at UVA, but eventually made his way back home to Tampa. Ever since then, he’s been an active investor in technology companies. Some of his investments were incredibly successful and some were not. Each investment he made, however, provided him with new, valuable experience to learn from for the future. 

On today’s episode, Stuart shares both these successes and failures. He shares his personal journey as an investor along with some of the nitty-gritty details of how he makes those big decisions and his own journey along the way. 

So get ready to learn some new strategies regarding making investments and what to watch out for. 

Some Questions I Ask: 

• When and how did you start angel investing? (4:27)
• What do you look for in an investment? (5:50)
• What deal size do you look for? (8:00)
• What red flags do you look for when considering an investment? (11:12)
• How do you interpret the market when making investments? (12:57)
• What’s the most important part of due diligence? (20:31)

In This Episode, You Will Learn: 

• How Stuart made his first investment. (2:27)
• Why focusing on the entrepreneur when choosing an investment is crucial. (5:55)
• Why it’s important to be as real and authentic as possible in investment conversations. (11:24)
• How the market determines the potential for the business you invest in. (13:05)
• When to put more money into a company, and when to shut it down. (15:26)
• Why some of Stuart’s investments failed. (16:01)
• About the roles of communication and coachability in the investment industry. (19:52)

More about Florida Funders:

Website

Our Investment Process

LinkedIn

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Disruptive investments—such as investments in transformational technologies that utilize applied artificial intelligence—oftentimes turn out in one of two ways. They can soar—like Apple or Microsoft—or they can tank.

Today’s guest, Jake Seid, says that when downturn happens, you can’t lose your momentum. Sometimes the best companies are built after these downturns—don’t forget that.

Jake is the managing director at Stone Bridge Ventures. He’s a venture investor focused on investments around the Bay Area in California, but he also invests nationally. Generally, he focuses on investing in disruptive technologies.

So get ready to learn from some of Jake’s hits and misses in investing so far.

Some Questions I Ask:

• How did you first get involved in angel investing? (2:30)
• What’s important to you in a company that you want to invest in? (3:14)
• What was your biggest miss? (5:19)
• What do you look for in founders? (8:15)
• Will you make an investment even if you predict a need to change the company’s top leadership within a couple of years? (10:36)
• What do you hope to hear from a company regarding their exit strategy? (18:57)
• Where do you get your best deal flow? (21:51)

In This Episode, You Will Learn:

• Where Jake received strong mentorship in investing early on in his career. (2:34)
• What makes a company worth investing in. (3:26)
• How to create defensibility. (4:34)
• About Jake’s biggest mistake in his career. (5:25)
• About the pros and cons of a founder and a founding team. (8:24)
• How investors can add more than monetary value to the company. (13:20)
• Why Jake is willing to take risks on technology. (15:37)

Connect with Jake:

LinkedIn

Twitter

AngelList

More about Florida Funders:

Website

Our Investment Process

LinkedIn

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There are so many unknowns and so many what if? questions running through your head. It’s the same situation for both the entrepreneur and the investor. Entrepreneurs and investors alike have a goal in mind—and they need the other person in order to get there. It’s risky, but sometimes it’s totally worth it in the end.

Today’s guest is Zach Coelius. Zach has worked on both sides of the story. He is a four-time entrepreneur, but now that he’s sold his last company, he shifted to full-time angel investing. In this episode, Zach tells us all about his experiences of getting started in investing, what his strategies are, and how he has become so successful.

So get ready to learn about Zach’s journey so far. Along the way, ask yourself: what will it take for me to get started?

Some Questions I Ask:

• What do you like better: being an entrepreneur or being an investor? (2:04)
• How did you first get involved in angel investing? (3:34)
• Where do you get your deal flow in? (7:10)
• What are you looking for in an investment? (8:51)
• When investing, when do you look for in the founder of the company? (11:54)
• There’s a lot going on in technology today. What are you interested in? (14:57)
• What red flags do you look out for in investing? (16:28)
• How much do you get involved in your investments? (21:55)

In This Episode, You Will Learn:

• About both the dark and light sides of entrepreneurship and investing. (2:07)
• How Zach transitioned from entrepreneurship to angel investing. (3:38)
• About how Zach’s “lazy-helpful” work with Silicon Valley changed the course of his career. (7:14)
• How entrepreneurship experiences can change investment behavior. (8:58)
• Why the founder is what can make or break the choice to invest. (12:10)
• Why Zach gets as involved as possible in his investments. (22:00)
• Why pitch competitions are ineffective and inefficient. (24:12)

Resources:

Chaos Monkeys: Obscene Fortune and Random Failure in Silicon Valley by Antonio Garcia Martinez

Connect with Zach:

AngelList

LinkedIn

More about Florida Funders:

Website

Our Investment Process

LinkedIn

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Are you an entrepreneur searching for an investor?

What’s stopping you?

Here at Florida Funders, our goal is to scour the state of Florida, searching for the very best early-stage technology companies to find, fund, and help build up. We are dedicated to changing Florida from the “Sunshine State” to the “Startup State,” making this a great place to start and build a business.

On today’s podcast, we talk to Alex Sink. Recently, Alex decided to shift her career from politics to helping entrepreneurs bring their fantasies to reality. In this episode, we talk all about her investment journey, what her ideal investment is, and what red flags she watches out for.

What will it take for you to get started?

Some Questions I Ask:

·     How did you get involved in investing? (3:32)

·     What technology or business models do you like that influence your investing habits? (10:56)

·     What deal size do you look for? (13:46)

·     How do you look at follow-ons? (17:03)

·     What do you think of pitch competitions? (21:48)

·     How involved do you like to get in an investment? (23:33)

In This Episode, You Will Learn:

·     About Alex’s transition into investing and her early-stage strategies. (3:44)

·     How to figure out what to invest in as a beginner. (11:06)

·     How Alex chooses what to invest in. (13:54)

·     How Alex deals with investments falling through. (15:07)

·     How Alex evaluates whether or not to participate in follow-on investments. (17:05)

·     What makes & breaks investment presentations. (19:05)

·     Why more women should become investors. (25:16)

More About Florida Funders:

Website

Our Investment Process

LinkedIn

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