Chicago Capital

Madelyn Rutter @ TechNexus

Matt Castellini — Tue, 25 Oct 2022 16:31:11 -0500

Madelyn Rutter is the Director of Collaboration at TechNexus.

She supports the Venture Collaborative with everything founder and partner success. That means growth, incubation, marketing, branding, and community, and helping corporate innovators achieve their goals by inspiring them to connect with the right entrepreneurs at the right time.

S5E2: Rich Lee @ New Era ADR

Matt Castellini — Thu, 13 Oct 2022 20:01:58 -0500

Rich is the CEO and Co-Founder of New Era ADR, a VC-backed technology company saving precious time and money for individuals and businesses, bringing long-desired yet never-before-seen certainty and predictability to the legal dispute process, up to 90% reductions in time and cost, and revolutionizing how disputes are resolved in the U.S.

Previously, he served on executive teams of two VC-backed technology companies that he helped build and scale through rapid growth and one acquisition so far. Before that, he led market development in Asian markets for two companies.

Season 5, Episode 1: Anuraag Tripathi @ Manifest

Matt Castellini — Wed, 05 Oct 2022 13:06:22 -0500

Manifest enables seamless 401(k) transfers - maximizing retirement outcomes by reducing rollover administrative hurdles. Their team is building the infrastructure to digitize retirement transfers.

S4E19: Tommy Flaim @ Fox & Robin

Matt Castellini — Fri, 12 Aug 2022 16:34:52 -0500

Fox & Robin is an activewear brand that creates top quality products for all levels of activity, whether you're doing high intensity training or, well...not. As a Benefit Corporation, they are committed to conducting business in an ethical and transparent manner.

S4E18: Ira Weiss @ Hyde Park Venture Partners on the Current Market Downturn

Matt Castellini — Thu, 07 Jul 2022 08:40:54 -0500

Ira Weiss is the General Partner at Hyde Park Venture Partners, an early-stage venture capital firm focused on high-growth, mid-continent technology startups. Ira is also a Clinical Professor of Entrepreneurship and Accounting at The University of Chicago, Booth School of Business.

In this episode, we discussed the current market downturn and it's impact on early-stage investing.

S4E17: Jessica Schultz @ Amplify

Matt Castellini — Wed, 15 Jun 2022 15:16:44 -0500

Amplify offers end-to-end strategy, solution design and tactical execution of your optimal revenue solution.

Strategy: Refining your Go-To-Market (GTM) strategy based on your industry, customer profile, value prop and competitive position
Platform: Combining best in class processes, tools, and analytics to achieve and measure results
Talent & Enablement: Designing the optimal talent and enablement strategy for scalable growth
Channels: Implementing a targeted channel partner strategy to expand your pipeline

S4E16: Raj Datta @ oak9

Matt Castellini — Tue, 31 May 2022 21:09:24 -0500

oak9.io is the security leader for all things cloud native. Their platform finds, analyzes and automatically remediates cloud infrastructure security and compliance issues in real-time, continuously learning and monitoring infrastructure as code (IaC) as changes occur - the only cloud native security solution supporting devsecops throughout the entire development cycle.

oak9 bridges the gap between dev and security, ensuring dev workloads and architecture are secure by design, while giving security teams complete visibility into the changes dev teams are making day over day, sprint over sprint.

oak9 has raised capital from some of the top VC's in the world, including Menlo Ventures.

For more leanings on Infrastructure-as-code, please see:

S4E15: Connor Ryan @ Bridge Investments

Matt Castellini — Fri, 13 May 2022 05:03:59 -0500

With a background rooted in private equity and venture capital, Connor takes a data-driven approach to investing, but also enjoys observing cultural shifts in consumer behavior and applying those learnings to new investment themes. Connor works closely with management teams to gain insights and improve performance and enjoys the challenge of understanding complex businesses. Connor is a University of Notre Dame graduate and earned his MBA from the Kellogg School of Management.

Bridge is a Chicago-based early stage venture fund with a split focus on SaaS and Consumer Brands across a diverse set of end markets. Select portfolio companies include InGoodTaste, EarlyBird, Mack Weldon, Simple Mills, Jiobit, PartySlate, Interior Define, haku, and ConverseNow

S4E14: Tessa Flippin @ Capitalize VC

Matt Castellini — Fri, 29 Apr 2022 15:12:01 -0500

Tessa Flippin is the Founder and Managing Partner of Capitalize VC, a pre-seed and seed stage VC fund purpose-built to reduce the racial wealth gap by investing in early-stage Black and Latinx founders, while simultaneously creating access for diverse LPs.

Tessa began her career in venture capital as a venture investor at TechNexus, a Chicago-based fund, where she invested in enterprise SaaS technologies at the seed stage. She went on to join Genius Guild Greenhouse Fund as a Venture Capitalist in Residence, investing in Black founders in fintech, health tech and connectivity.

Prior to venture capital, Tessa founded La Plataforma, a fintech payments platform, sending international money transfers throughout Latin America.

Tessa attended Stanford University for undergrad where she ran Track and Field and joined Alpha Kappa Alpha Sorority, Inc. She went on to receive her MBA from Columbia Business School where she studied entrepreneurship, venture capital and social impact.

Tessa actively serves on the board of BLCK VC Midwest and the advisory board of Chicago:Blend working to bring diversity to the Midwest tech ecosystem. She is also a member of the Cap Table Coalition investment committee.

S4E13: Daniel Estrada @ 86 Repairs

Matt Castellini — Sun, 10 Apr 2022 14:39:28 -0500

86 Repairs is the repair and maintenance management platform built for the restaurant industry. Our tech-enabled solution includes on-demand repair management and preventative maintenance. With 86 Repairs, restaurants have access to data-driven insights and 24/7 support to control their facilities, reduce their R&M costs, and spend less of their team's time on equipment repairs.

S4E12: Jordan Gal @ Rally

Matt Castellini — Tue, 29 Mar 2022 05:27:13 -0500

Jordan is the CEO and Founder of Rally, a headless checkout for modern brands. The company offers ecommerce merchants a better converting, more profitable, one-click checkout.

Rally is on a mission to bring power back to merchants and app developers by equipping them with a headless and fully optimized one-click checkout solution. Rally is central to the modern headless ecommerce ecosystem bridging front- and back-end platforms, and plays a critical role in creating a seamless checkout experience for customers. Rally’s team of industry leaders pioneered the post-purchase offer technology for DTC brands, driving over $200m in post-purchase revenue and processed $3B in sales. Rally appreciates a decentralized ethos and is merchant and revenue-focused, always.

Jordan's podcast, Boostrapped Web, can be found here!

https://bootstrappedweb.com/

S4E11: Tom Zhang @ Zenblen

Matt Castellini — Fri, 11 Mar 2022 18:18:33 -0600

Tom Zhang is the Co-Founder and CEO of Zenblen. Zenblen is developing a tech-enabled smoothie bar that blends healthy, nutritionist-curated smoothies right in front of the consumer. They partner with high-frequented locations, such as gyms and office buildings, in our mission to make healthy-eating more convenient in everyone's daily routines

S4E10: A Year in Review

Matt Castellini — Fri, 04 Mar 2022 12:30:04 -0600

Declan Zidar and I sit down to discuss the past, present, and future of Chicago Capital. Tune in for a deep-dive on:

Our professional backgrounds
Starting a Podcast
The catalyst for Chicago Capital
Views on Chicago Startup Ecosystem
Tips for breaking into VC (Pre-MBA and Post-MBA)
General early-career advice
Books and Resources we love

Special thanks, again, to Kevin Daly for all of this work on the show. Also thank you to everyone who has tuned in and agreed to hop on the show. Cannot wait for what's next.

Take it easy.

S4E9: Thru Shivakumar @ cohesion

Matt Castellini — Fri, 25 Feb 2022 20:05:24 -0600

Thru Shivakumar is the CEO & Co-Founder of cohesion, a smart building SaaS platform at the intersection of green, healthy, and operationally efficient buildings for CRE.

With its building experience app, cohesion provides a secure, converged IoT-enabled software solution that unites core building workflows, optimizes portfolio management, and generates actionable insights to increase profitability and create better tenant experiences.

The company combines a wide range of capabilities necessary to support the Intelligent Building Platform that include the Internet of Things, Data Analytics, Artificial Intelligence, Cloud and Mobile technologies and Machine Learning. Its solution offers a breadth of features for various user roles, comprising the owner, operator, tenant manager, and tenant in a single platform.

cohesion's deep building and technology expertise stem from its birth heritage at a global engineering and design firm, combining strategic product elements, including architecture, mechanical, electrical, plumbing, cutting-edge information technology and software engineering capabilities

This episode is brought to you by World Business Chicago. As the City of Chicago’s economic development organization, World Business Chicago drives inclusive growth and opportunity for our local tech, innovation, and startup ecosystem. They recently announced the 2022 Chicago Venture Summit Future-of-Food, their new flagship conference to highlight why Chicago leads as a the global capital for food innovation. Follow World Business Chicago on LinkedIn and Twitter for event details and other related news about our city’s economic progress.

S4E8: Jithendra Palasagaram @ Part Analytics

Matt Castellini — Fri, 18 Feb 2022 15:35:49 -0600

Jithendra Palasagaram is the CEO and Founder of Part Analytics, a Venture-backed startup focused on transforming direct material procurement by digitizing manual processes and harmonizing data from multiple disparate sources. Its AI-powered supply management solution with a modern and intuitive UI enables smarter data-driven decision making to optimize cost and uncover hidden supply risk.

S4E7: Shawn Ellis @ Distributed Ventures on Transitioning to VC From Consulting and Banking, Operating vs. Investing, & The Strategy Behind Distributed VC

Matt Castellini — Wed, 02 Feb 2022 13:14:28 -0600

Distributed Ventures invests in companies that are transforming the future of risk across Insurtech, Fintech and Healthtech & Benefits. Their mission is to find, fund and work successfully with visionary entrepreneurs. They target companies seeking Seed to Series B investments that can benefit from NFP and other LP's distribution, human capital, and unique assets to accelerate their growth. Distributed Ventures has offices in both Chicago and New York.

We Discussed:

Transitioning from Consulting and Investment Banking to Venture Capital
Startup Experience vs. Investing
Distributed Ventures and their Insurtech, Fintech, and Health Tech focus

S4E6: Sonny Tai @ Actuate

Matt Castellini — Fri, 28 Jan 2022 16:04:55 -0600

Actuate's AI software turned existing security cameras that can automatically identify threats and occupant behavior patterns to support security and facilities management teams.

Our core capabilities include: gun detection, intruder detection, crowd / loitering detection, social distancing detection, and mask detection.

Backed by Tribeca Venture Partners, Scribble Ventures, Bling Capital, Upside Partnership, Tensility Venture Partners, and the University of Chicago.

S4E5: Janice Tam Co-Founder & CEO @ TrueToForm

Matt Castellini — Thu, 13 Jan 2022 22:19:22 -0600

TrueToForm is a body scanning and data management platform that helps businesses create and sell clothing that fits.

Their mobile application generates highly accurate avatars for apparel design and fitting. They use proprietary algorithms and computer vision to capture body shape and size in 3D, along with full body measurement extraction. Anywhere, any time.

They help businesses get access to the body data they need to improve fit, expand reach, and reduce waste across the product creation lifecycle.

S4E4: Teresa Wang @ Heyday Fitness

Matt Castellini — Thu, 06 Jan 2022 19:40:32 -0600

Heyday is the first interactive strength home gym for the 60+ to train for real life. Strength is the most important workout for better aging. Heyday is revolutionizing aging experience by making strength training safe, effective and fun. With low impact workouts, workout parties, encouraging trainers and personal resistance guidance, Heyday redefines strength training to be more inclusive and social, without compromising intensity.

The company is founded in 2021 and is headquartered in San Francisco.

S4E3: Lisa Bubes @ Garmentier

Matt Castellini — Wed, 15 Dec 2021 09:03:40 -0600

Garmentier is the first retail technology platform to transform the 1:1 shopping experience into scalable selling technology. They are an enterprise software company with marketplace capabilities, giving superpowers to stylists, salespeople and retailers alike.

Garmentier enables a new level of personalization and humanization in omni-channel customer experiences. They remove growth roadblocks, open exciting new sales channels, and help our customers grow their businesses by delivering an unparalleled shopping experience: all in 1 simplified platform.

They're fundraising - and hiring! Contact them: info@garmentier.co

S4E2: Jason Starr @ CompanyFirst on DTC Investing, State of Consumer, & Consumer Brands in Chicago

Matt Castellini — Thu, 09 Dec 2021 23:07:09 -0600

Jason Starr is the founder of CompanyFirst, a venture capital firm focused on investing in and building emerging consumer brands and companies. Before CompanyFirst, Jason was the fund manager at CircleUp in San Francisco, through which he invested in dozens of consumer ventures. Prior to CircleUp, Jason spent over eight years at Winona Capital Management, a consumer-focused private equity firm in Chicago with over $300 million under management. Before Winona, Jason worked at venture capital firm Opus Capital in Silicon Valley and was a founder or early employee at several high-tech start-ups in Denver including BoldTech Systems, a “Deloitte Tech Fast 50” and “Inc. 500” company that was acquired by Perficient (NASDAQ PRFT). Prior to his entrepreneurial ventures, Jason spent over five years at Andersen Consulting (now Accenture) where he was a project manager and software engineer. Jason graduated from the University of Chicago Booth School of Business with an MBA and holds a BSBA and MAS from the University of Denver, where he was an alumni scholar and graduated summa cum laude.

Season 4, Episode 1: Ben Johnson @ Spruce

Matt Castellini — Fri, 03 Dec 2021 15:39:09 -0600

Ben Johnson is the Founder and CEO of Spruce, which develops a platform that enables individuals to receive services in their homes through a mobile app. From full housekeeping to a quick tidy-up or a dog walk for your furry friend, Spruce is available to residents on-demand. At the end of 2020, Spruce raised an $8M Series A, led by Mercury Fund.

Ben spent a little over 5.5 years at ING working on digital banking before starting Spruce. He attended the University of Texas at Austin and got his MBA from the University of Chicago Booth School of Business.

Earlier this year, the company purchased The Minte, a Chicago-based startup known for their hotel-style apartment cleaning services, which also enabled the Spruce team to officially expand into the Chicago market. And now, after tallying up their various wins from the year so far, including a 400% YOY growth in revenue, the Spruce team has announced that they are officially the nation's largest tech-enabled apartment amenity provider, serving more than 450,000 apartment homes in 15 markets across the country

S3E20: Christopher Deutsch @ Lofty Ventures on State of Chicago Tech, Origins of Lofty Ventures, & Evaluating Founders

Matt Castellini — Tue, 30 Nov 2021 20:13:29 -0600

Chris Deutsch is the Founder of Lofty Ventures, which works with passionate creators, disruptive enterprises, and forward-thinking organizations to help them change the world. Focused on first-check to seed investments in early-stage entrepreneurs based in Chicago. 84 percent of Lofty's 61 startups are based in Chicago, and 74% are led by minority founders.

In this episode, we covered:

Pathway to Entrepreneurship and VC
Angel Investing
Re-Founding TeaBot
The Status of the Chicago VC ecosystem

And much more.... Please Enjoy!

You can find Chris on his Linkedin & Twitter. You can also find Lofty Ventures on Linkedin, Twitter, their website.

In 2021 alone, local founders have raised more than $5 billion in VC dollars – making Chicago a national destination for founders, investors, and innovators. As the City of Chicago’s economic development organization, World Business Chicago drives growth and opportunity for our local tech economy and innovation ecosystem through its flagship programs: the Chicago Venture Summit, Startup Chicago, ThinkChicago, and Venture Engine. Learn more via WorldBusinessChicago.com

S3E19: George Khalife @ Let's Grab Coffee Podcast

Matt Castellini — Fri, 12 Nov 2021 16:35:21 -0600

George Khalife is the Vice President, Midwest U.S. at TMX Group, a Canadian Financial Services Company that administers global markets and creates digital communities and analytic tools to help businesses, traders, and investors fund, grow, and succeed. George is also the Host & Founder of Let’s Grab Coffee, a podcast that strives to interview successful people from many fields.

In this episode, we covered:

Starting a Podcast
Toronto & Chicago
The Mandate of TSX
Prodcast Strategy & Distribution

And much more.... Please Enjoy!

You can find George on his Linkedin, Website, Blog, & Twitter. You can also find TMX Group on Linkedin, Twitter, their website and Let’s Grab Coffee on Linkedin, Apple Podcasts, and their website.

S3E18: John Allen @ Lava

Matt Castellini — Sat, 06 Nov 2021 13:18:24 -0500

Lava is a mobile app that empowers you to create, share, & discover social audio

Your voice has a lasting impact on Lava. Record and share social audio seamlessly on our mobile app then go viral through the global feed that highlights audio clips from creators around the world. Build your audience through your profile and follow along as new communities form around topics such as technology, art, sports, and science.

With Lava, anyone has the potential to be a social audio creator without equipment, commitment, or investment. Simply download Lava: Social Audio on iOS or Android to connect with friends, share your thoughts, and find your voice.

S3E17: Nick Cromydas @ Hunt Club

Matt Castellini — Sat, 30 Oct 2021 09:39:28 -0500

Hunt Club is a new category of search firm.

Cold calling, spamming on Linkedin, impersonal mass reach out, treating candidates like a transaction v. a person... These methods no longer work in today's fight to attract the best talent.

Hunt Club helps companies find amazing passive talent + give well-connected individuals (influencers) a direct channel to help their network find amazing jobs. Hunt Club delivers white-glove service throughout the entire process.

Referrers get rewarded, candidates get great opportunities and companies land passive talent. Everyone wins.

S3E16: Lindsay Knight @ Chicago Ventures on The Platform Model in VC & Chicago:Blend

Matt Castellini — Fri, 29 Oct 2021 10:37:09 -0500

Lindsay Knight manages CV’s Platform, or the firm’s “post-investment” team. She works directly with the firm’s 50+ active portfolio companies on matchmaking talent; connecting into customers; marketing, communication and PR; and building community, content, and events to help scale up and skill up more efficiently. She’s also a Kauffman Fellow, Class 23.

Prior to joining Chicago Ventures, Lindsay spent time at Ocean Tomo, an intellectual property merchant bank, where she was part of the team that launched the industry’s first live patent auctions. She later joined CHOUmedia as Vice President, where she worked with clients in the IP industry on marketing strategy and execution.

We discussed:

-Her early career in Marketing and Comms

-The Platform Model in VC

-Her daily workstreams at Chicago Ventures

-Founding Chicago:Blend

In 2018, Lindsay launched the non-profit Chicago:Blend, a collaborative effort of venture capitalists in Chicago who know that diverse teams and inclusive environments are critical foundations for both the startups we invest in and our own venture firms. She’s a former Chair of the VC Platform Global Community and serves on the Governing Board at Lookingglass Theatre, a Tony-award winning theatre that focuses on the spectacular and the physical. She graduated from the Miami University Honors Program with degrees in English/Journalism and Strategic Communication.

S3E15: Patrick Larsen @ ZenLedger.io

Matt Castellini — Fri, 22 Oct 2021 15:44:34 -0500

Patrick Larsen is the CEO and co-founder of ZenLedger.io, a blockchain saas company that delivers tax and accounting services to individual and cryptocurrency investors as well as to CPAs and crypto hedge funds.

The company works with Big 4 accounting firms (high net worth practice), crypto whales, CPAs, and everyday traders. Zenledger has integrations with hundreds of exchanges and wallets and thousands of cryptocurrency tokens/coins.

Zenledger is hiring in software development (front and back end), product management, customer service, brand and analytical marketing, and business development.

Investors include: Vestigo Ventures, Castle Island Ventures, Sally Nordstrom, and Ben Davenport.

www.ZenLedger.io

S3E14: Peter Johnson @ Jump Capital on Jump Capital's New $350mn Crypto Fund, & Stablecoins Investment Thesis

Matt Castellini — Wed, 20 Oct 2021 10:12:43 -0500

Peter Johnson is a Partner at Jump Capital, a venture capital firm that invests in data-driven software startups in the FinTech, IT & Data Infrastructure, B2B SaaS, and Media industries. They also invest in crypto startups and projects that are redefining what is possible in an open financial and decentralized network future. Jump makes high-conviction investments and has assisted in the scaling of some of the industry's leading businesses.

In this episode, we covered:

Crypto
Jump Capital’s New Fund
Stablecoins
Cross-Border Transactions
Advantages in the Chicago Market

And much more.... Please Enjoy!

You can find Peter on his Linkedin & Twitter and Jump Capital on Linkedin, Twitter and their website.

Jump Capital’s Insights page and his blog on Stablecoins.

S3E13: Dominic Go @ Tambr

Matt Castellini — Fri, 15 Oct 2021 15:01:04 -0500

Dominic Go is the founder & CEO of Tambr, a streaming music service built for enhanced social connection while empowering the artistic community.

S3E12: Alyssa Jaffee @ 7wireVentures on Trends in Digital Healthcare & Technology, & the Healthcare Industry in Chicago

Matt Castellini — Thu, 14 Oct 2021 11:29:35 -0500

Alyssa Jaffee is a Partner at 7wireVentures, an early-stage healthcare venture fund. She focuses on digital healthcare and technology-enabled services that enable customers to be better stewards of their health in today's shifting healthcare ecosystem. Alyssa serves on the boards of Higi and Ayogo Health, as well as Zerigo Health, NOCD, RecoveryOne, and Jasper Health as an observer.

In this episode, we covered:

7wireVentures Thesis
Trends in digital healthcare and technology
Healthcare Industry in Chicago

And much more.... Please Enjoy!

You can find Alyssa on his Linkedin & Twitter and 7wireVentures on Linkedin, Twitter and their website.

S3E11: Tom Shea @ Adgile Media Group

Matt Castellini — Fri, 08 Oct 2021 17:41:17 -0500

Tom Shea is the Co-Founder and COO of Adgile Media Group, the first ever tech-enabled, nationwide truckside advertising company. With data at the center of all that we do, Adgile delivers advertisers the biggest bang for their advertising dollar.

S3E10: Justin Strausbaugh @ Lakeshore Ventures on Alumni Ventures Group, State of Venture Capital, & Deep Tech Trends

Matt Castellini — Fri, 08 Oct 2021 08:32:38 -0500

Justin Strausbaugh is the Founder and Managing Director of Lakeshore Ventures, which is part of the Alumni Ventures Group family of funds, one of the most active venture firms in the world with +$500 million AUM, 700+ portfolio companies and a community of 550K alumni from other top tier universities.

Alumni Ventures was the #1 most active venture capital investor in the US in 2020 and is comprised of 20+ funds from the alumni communities of leading universities (including Stanford, Harvard, University of Chicago, MIT, and others). AVG co-invests alongside top leading investors and complements them with a network of 550K+ alumni to help portfolio companies with customer introductions, fundraising, recruiting, and identifying advisors.

The philosophy is to provide a frictionless investment process for startups and co-investors while bringing a force-multiplying network that gives entrepreneurs a competitive advantage.

S3E9: Troy Henikoff @ MATH Venture Partners on Ted Lasso, Early-Stage Financial Modeling, & Techstars Chicago

Matt Castellini — Wed, 29 Sep 2021 16:29:23 -0500

Troy Henikoff is a Managing Director at MATH Venture Partners, a Chicago-based venture capital business that invests in startups and early-stage companies.

In this episode, we covered:

Ted Lasso
VC as an Ex-Operator
MATH 100
Setting Numeric Goals for Founders
Early-stage Financial Modeling
Techstars in Chicago

And much more.... Please Enjoy!

You can find Troy on his Linkedin & Twitter and MATH Venture Partners on Linkedin and their website.

We are proud to be sponsored by World Business Chicago, the City of Chicago’s public-private economic development agency.

The 5th Annual Chicago Venture Summit was officially sold out. 450 plus VC and start-up founders, investors and innovators connected over the three-day flagship venture capital conference led by World Business Chicago, the City of Chicago, and sponsors. Follow World Business Chicago on LinkedIn and Twitter for news, announcements, and data from this week’s Summit, and for news and announcements from the city’s tech, innovation, and venture ecosystem.

S3E8: Nathan Rosenstock @ Crafty

Matt Castellini — Mon, 27 Sep 2021 10:04:24 -0500

In 2015, Nate and his three close friends co-founded Crafty to help companies create welcoming and healthy workplaces through a thoughtful food and beverage offering.

Crafty’s platform provides a full-service food & beverage management experience: their on-site teams streamline daily operations, their Account Management teams regularly evolve their client's offering, their technology streamlines oversight and reporting across all locations, and their entire organization is constantly finding ways to surprise and delight their clients with new products, a beautiful aesthetic, and a warm smile from their team.

S3E7: Samara Mejia Hernandez @ Chingona Ventures on Chingona's Investment Mandate, Raising Her First Fund, & Career Advice for VCs

Matt Castellini — Wed, 22 Sep 2021 10:41:18 -0500

Samara Mejia Hernandez is the Founding Partner and Managing Director of Chingona Ventures, a Venture Fund that focuses on rapidly changing sectors and founders with experiences that uniquely position them to build startups in underserved growth markets.

In this episode, we covered:

Salsa Dancing to VC
The COVID Effect
The Growing Interest in VC
Chingona’s 5P Due Diligence Framework
Advice for Aspiring VC’s

And much more.... Please Enjoy!

You can find Samara on her Linkedin & Twitter and Chingona Ventures on Linkedin, Twitter, and their website.

Samara’s Organization Recommendations: Chicago:Blend, Angeles Investors, and Latinx VC.

S3E6: Konrad Waliszewski @ Tripscout

Matt Castellini — Mon, 20 Sep 2021 05:42:49 -0500

Konrad Waliszewski is the CEO & Co-Founder of Tripscout - the #1 ranked trip planning app and a Top 5 content app in the AppStore with millions of users, 15M+ Instagram followers, and $6m raised in venture capital. He has visited approximately 100 countries and Forbes named him “the modern day Marco Polo.” Positioned at the intersection of consumer trends and travel tech, Konrad is a regular speaker and commentator on major media outlets about the future of travel.

S3E5: Victor Pasucci @ Energy Capital Ventures on the State of ESG Investing, Transitioning from Law to VC, & the Maturation of the Chicago Early-Stage Ecosystem

Matt Castellini — Wed, 15 Sep 2021 21:22:09 -0500

Vic Pascucci is the Managing Partner of Energy Capital Ventures, a Venture Fund dedicated to the natural gas industry's ESG imperatives and digital transformation. They provide the newest ideas and technological advances to the natural gas market by investing in category-defining companies.

In this episode, we covered:

State of ESG Investing
Transitioning from Law to VC
The Need for Curiosity in Venture
Fundraising in 2021

And much more.... Please Enjoy!

You can find Vic on his Linkedin & Twitter and Energy Capital Ventures on Linkedin, Twitter, and their website.

Manifold Group is a venture holding company based in Chicago with offices in Dallas, Los Angeles, and soon Atlantic Canada. Early stage private investments represent an extraordinary investment opportunity, but existing investment models in the space leave much to be desired.Manifold is a new model for growth in the new economy, designed to create and capture value at the early stage through synergies across its venture fund, incubation and acceleration studio, and advisory firm. Learn more about Manifold at https://www.manifold.group.

The Mid-Year Review

Matt Castellini — Fri, 10 Sep 2021 10:57:19 -0500

We have hit the official 6-month mark on the show. We decided to round up the most downloaded episodes and my personal favorite moments from each of those episodes. I think the following excerpts do a good job of encapsulating the amazing and brilliant people that I have been lucky to interview in the past 6 months.

This episode features:

Ezra Galston @ Starting Line (2:48)
Trey Calver @ Michael Best (6:06)
Jackson Bubala @ Motivate Venture Capital (8:46)
Ari Perlin @ Vaizian (19:56)
Joe Dwyer @ Manifold Group (22:09)
Jackie Dimonte @ Chicago Ventures (31:28)
Rick Desai @ Listen Ventures (36:55)
Gale Wilkinson @ Vitalize Venture Capital (39:19)
Cristin Pacifico @ TechNexus (41:16)
Ira Weiss @ Hyde Park Venture Partners (46:25)
Jason Heltzer @ Origin Ventures (49:30)
Kathleen Brown @ buddhi (58:06)

A sincere thank you to every one of my guests over the past six months. This has been an incredible journey and I owe each and every one of you for that.

S3E5: Yelena Shkolnik @ Jump Capital on Recipe for Innovation, State of Sports Betting, & Streaming in '21

Matt Castellini — Wed, 08 Sep 2021 21:01:21 -0500

Yelena Shkolnik is a Partner at Jump Capital, a venture capital firm concentrating in Series A/B and growth stage investments, with a thesis-driven and sector-focused approach. Jump makes data-driven technology investments in the FinTech, B2B SaaS, IT Infrastructure, and Media industries.

In this episode, we covered:

Her Dreamworks background and a walk down Hollywood
Jump Capital and their thematics driven Thesis
The recipe for innovation
Sports betting (and generational differences)

And much more.... Please Enjoy!

You can find Yelena on her Linkedin & Twitter and Jump Capital on Linkedin, Twitter, and their website.

S3E4: Neil Sikka @ A1Logic

Matt Castellini — Mon, 06 Sep 2021 09:14:16 -0500

A1Logic offers A1FILO Data Breach Prevention. A1FILO uniquely secures your data "in use", along with data "at rest" and "in transit".
It stops data breaches from

Malicious Insiders
Compromised Devices
Compromised Networks

S3E3: Steve Sanger @ Evolv on State of Foodtech, Corporate VC, & Scaling Grubhub

Matt Castellini — Thu, 02 Sep 2021 18:19:04 -0500

Steve Sanger is the General Partner of Evolv Partners, a $100 million corporate venture fund that invests in early-stage digital businesses that are changing the food sector.

In this episode, we covered:

Scaling GrubHub
Business Development within Startups
State of Foodtech
Corporate VC
Breaking into VC

And much more.... Please Enjoy!

You can find Steve on his Linkedin & Twitter and Evolv Ventures on Linkedin, Twitter, and their website.

Steve’s article on Life in Business Development at a Startup. How it’s Different From Sales.

S3E2: Kathleen Brown @ buddhi

Matt Castellini — Fri, 27 Aug 2021 22:47:36 -0500

buddhi is the digital platform reimagining support for people coping with cancer. The company bridges the disconnects caused by cancer through content, community and curated products. They are on a mission to support healing across your entire cancer experience — regardless of time, diagnosis or geography. Because everyone could use a bud.

Season 3, Episode 1: Sean Johnson @ Manifold Group on Venture Studio Models, Operational Leverage, State of Podcasts

Matt Castellini — Wed, 25 Aug 2021 21:30:01 -0500

Sean Johnson is the Founding Partner of Manifold Group, a Chicago-based venture holding company. He is also a Partner at Founder Equity and an Adjunct Professor at the Northwestern University Kellogg School of Business.

In this episode, we covered:

The Studio Model of Manifold
Finding Operational Leverage in Startups
Marketing Through Podcasts

And much more.... Please Enjoy!

You can find Sean on his Linkedin, website & Twitter and Manifold Group on Linkedin, Twitter, and their website.

Sean’s podcast: The Disruptors - Innovation, Startups, and Growth

S2E20: Matt Silver @ Forager

Matt Castellini — Fri, 20 Aug 2021 18:56:51 -0500

Matt Silver is the founder and CEO of Forager, a logistics tech company that simplifies the process of shipping goods between the U.S., Mexico, and Canada. Before founding Forager in late 2018, Silver spent over a decade at Coyote Logistics where he led the expansion of their business in Mexico and Canada. Now with purpose-built technology and industry expertise, Forager and Silver are setting the new standard for cross-border shipping.

He brings over a decade of industry experience, and invaluable expertise having worked in roles spanning every aspect of the logistics business. Under his leadership and vision Forager is working to innovate and automate the movement of freight across The United States, Mexico and Canada by developing ground-breaking technology that will transform the cross-border logistics industry and offer customers a fast and seamless solution for international shipping.

S2E19: Jason Heltzer @ Origin Ventures on Breaking into VC, Mixing Disciplines as a VC, & Chicago's Diversified Economy

Matt Castellini — Wed, 18 Aug 2021 13:19:00 -0500

Jason Heltzer is the Managing Partner at Origin Ventures, a Digital Native economy-focused early-stage venture capital firm that invests in software and marketplace startups. He is also an Adjunct Professor of Entrepreneurship at the University of Chicago Booth School of Business.

In this episode, we covered:

Mixing Disciplines as a VC
Origin’s Investment Mandate
Breaking Into VC
Chicago’s Integrated Economy

And much more.... Please Enjoy!

You can find Jason on his Linkedin & Twitter and Origin Ventures on Linkedin, Twitter, and their website.

S2E18: Tim Speicher @ Buoy

Matt Castellini — Fri, 13 Aug 2021 11:49:23 -0500

Buoy is designing the simplest, yet most comprehensive revenue management tools for the global vacation rental market

S2E17: Kurt Johnson @ 11.2 Ventures on Venture Builder Studios, Following Your Passions, & The Sales Process in VC

Matt Castellini — Wed, 11 Aug 2021 18:41:40 -0500

Kurt Johnson is the Managing Partner, CEO, and Founder at 11.2 Ventures, LLC, a Venture builder studio specializing in artificial intelligence startups. Kurt is also the Managing Partner & Founder at Trivium Fund and a Venture Partner at Purple Arch Ventures.

In this episode, we covered:

Transferable Sales Skills for VC
His Passion for Writing
11.2 Venture’s Area of Focus
Venture Builder Studios

And much more.... Please Enjoy!

You can find Kurt on his Linkedin and 11.2 Ventures, LLC on their website and Linkedin.

S2E16: Ira Weiss @ Hyde Park Venture Partners on Chicago Unicorns, Early-Stage Valuations, and Academia in VC

Matt Castellini — Wed, 04 Aug 2021 18:10:19 -0500

In this episode, we covered:

From Shoe Salesman to VC
Developing a Market View Advantage
Metrics in Valuations
Keys to Success for Unicorns
Improving Chicago’s Ecosystem

And much more.... Please Enjoy!

You can find Ira on his Linkedin & Twitter and Hyde Park Ventures on their website, Twitter, and Linkedin.

Ira’s Favorite Thought Leadership/Resources: The 20 Minute VC, a16z Podcast, Fred Wilson, Brad Feld, Mark Suster, & Ajay Agarwal’s Writing

S2E15: Ryan Walsh @ Valqari

Matt Castellini — Fri, 30 Jul 2021 15:47:23 -0500

Valqari's patented intelligent mailbox that accepts manned and unmanned deliveries, such as drones and autonomous vehicles.

Valqari Features and Benefits:

Vault feature allows traditional deliverers to make theft-free deliveries

Allows customers to make direct returns to shippers.

Valqari's mobile application allows for customers to digitally sign for packages from anywhere in the world, reducing failed delivery attempts.

Valqari provides the infrastructure and communication for unmanned delivery modes to enable safe, secure, and reliable deliveries.

S2E14: Abhinaya Konduru @ M25 on Life as a Junior VC, Chicago Collaboration, and Early-Stage Analysis

Matt Castellini — Wed, 28 Jul 2021 21:03:02 -0500

Abhinaya Konduru is a Senior Associate at M25, a Chicago-based early-stage venture capital firm that focuses on Midwest-based startups. Abhinaya is also a Board Observer at Mission Control GG and an Associates & Analyst Moderator at Women in VC.

In this episode, we covered:

From YouTube to VC
Her Life Thesis
M25’s Scoreboard Analysis
Collaboration in the Ecosystem
Lessons Learned as a Young VC

And much more.... Please Enjoy!

You can find Abhinaya on Linkedin & Twitter and M25 on their website, Linkedin, & Twitter.

Abhinaya’s Medium & Blog about the Four Lessons from being a VC out of Undergrad

Sushi Restaurant Recommendations: ARAMI & SUSHI-SAN

Content Recommendations: The Sandhill Newsletter

S2E13: Ari Perlin @ Vaizian

Matt Castellini — Fri, 23 Jul 2021 14:27:55 -0500

Ari Perlin is the Co-Founder and CEO of Vaizianl, a medical software company that helps ER doctors rapidly diagnose and treat patients by statistically assessing clinical data. Their patent-pending technology reduces the medical risk and waste commonly associated with ambiguous ER conditions like chest pain.

S2E12: Gale Wilkinson @ Vitalize Venture Capital on Angel vs VC Investing, Future of Work & Education, and Increasing Diversity in Tech

Matt Castellini — Wed, 21 Jul 2021 11:37:09 -0500

Gale Wilkinson is the Founder & Managing Partner at Vitalize Venture Capital, a seed-stage investment firm focused on the future of work and education. Gale is also a Board member at Chicago:Blend, a NFP dedicated to increasing diversity in tech & VC. She contributes to a YouTube series named Talking Venture & even offers office hours for founders and aspiring VCs.

In this episode, we covered:

Investing with Angel Investors vs. Venture Capital
Focusing on the Future of Work & Education
The Importance of Data in Investing
Themes Coming out of 2020
Increasing Diversity in Startups & Venture Capital

And much more.... Please Enjoy!

You can find Gale on Linkedin, her website, & Twitter and Vitalize Venture Capital on their website, Linkedin, & Twitter.

S2E11: Leo Mindyuk @ ML Tech

Matt Castellini — Fri, 16 Jul 2021 16:28:57 -0500

Leo Mindyuk is the CEO & Founder of ML Tech, a FinTech startup building the next-generation trading platform within the crypto asset space. ML Tech's vision is to combine colocated trading infra speeds with cloud intelligence into a single “package” and make it accessible to seasoned quant researchers worldwide. Their platform leverages cutting-edge AI solutions and allows researchers to produce new strategies at an industry-leading pace. Strategies can rely on their robust HFT capabilities to generate steady and consistent returns.

S2E10: Brian Luerssen @ Draftbit & LongJump on Founder-Led VC, The Chicago Startup Ecosystem, and Low-Code/No-Code

Matt Castellini — Wed, 14 Jul 2021 10:53:28 -0500

Brian Luersson is the Co-Founder of Draftbit & General Partner at LongJump. Draftbit is a Chicago Startup that helps create, customize, and launch mobile apps all from a browser, with source code included. LongJump is a Chicago-based founder-led fund that invests in the next generation of entrepreneurs. They offer funding, connections, and community to help creators take the first steps toward developing scalable, fast-growing businesses.

In this episode, we covered:

The Origin of Draftbit
Low-Code & No-Code Businesses
Balancing Entrepreneurship & Venture Capital
Founder-Lead Venture Capital
The Chicago Startup Circle

And much more.... Please Enjoy!

You can find Brian on Linkedin & Twitter, Draftbit on their website, Linkedin, & Twitter, and LongJump on their website, Linkedin, & Twitter.

Restaurant Recommendation: J.P. Graziano for the Mr. G Sandwich.

S2E9: Sebastian Rivas @ Andes STR (2021 NVC Winner)

Matt Castellini — Fri, 09 Jul 2021 19:24:35 -0500

Sebastian Rivas is the Founder & CEO at Andes STR, a PropTech startup dedicated to providing investors turnkey access to Short Term Rentals as an asset class.

Sebastian led the Andes team through Polsky Center's New Venture Challenge, achieving 1st place in the largest competition to date and obtaining commitments for over USD $1.8M during fundraising

S2E8: Prashant Shukla @ Origin Ventures on Seed v. Series A, Cameo's Ascendance, & the Future of Chicago Tech

Matt Castellini — Wed, 07 Jul 2021 10:29:15 -0500

Prashant is a Vice President at Origin Ventures, joining the firm as Senior Associate in May 2017. He serves as a board director for Origin portfolio company BlackCart and board observer for 15Five, Blueboard, Glimpse, Everee, Pronto, Measured Insurance, and Trala.

Prashant started his career at Bain & Company. During his time at Bain, he advised telecom, healthcare, & education clients, but spent most of his time on a large technology client dealing with strategic questions around emerging technologies. After Bain, he joined San Francisco-based startup Metromile in 2012 as the first product manager, building a pay-per-mile auto insurance product. Prashant helped scale the company to over three hundred employees as it took in over $200m in venture capital financing.

In this episode, we covered:

Politics vs. Venture
Value-Add Investing
Signs of Product-Market Fit
The emergence of the Creator Economy
Chicago’s Ecosystem

And much more... Please Enjoy!

You can find Prashant on Linkedin & Twitter and Origin Ventures on Linkedin, Twitter, and their website.

Restaurant Recommendations: RPM, Ema, Aba, Momotaro, Galit, The Spice Room, Vajra, Roister, and Alinea.

S2E7: Dip Majumder @ Neural Trend

Matt Castellini — Fri, 02 Jul 2021 15:53:05 -0500

Neural Trend is on a mission is to help retailers manage products that maximize sales while reducing go-to-market time.

Using cutting-edge AI technology, Neural Trend offers unparalleled data analytics in record time, equipping their clients with the power to match product design with market demand, quickly and accurately.

The strength of Neural Trend technology at your fingertips: their practical and customizable user interface empowers you to easily access our deep learning market analytics and helps you apply them directly to your product line.

With Neural Trend, you have the power to expedite, simplify, and strengthen your retail process.

S2E6: Ezra Galston @ Starting Line on Resiliency, Starting Line Fund II, & the State of Chicago Tech

Matt Castellini — Wed, 30 Jun 2021 11:20:52 -0500

Ezra Galston is the Founding Partner at Starting Line, a Chicago-based early-stage venture capital firm that invests in leading consumer products and brands.

In this episode, we covered

Fundraising Resiliency
Starting Line Fund II
Building to Conviction
Post-Investment Value-Add
The Challenges of the VC Feedback Loop
State of Chicago Tech

And much more.... Please Enjoy!

You can find Ezra on Linkedin & Twitter and Starting Line on Linkedin, Twitter.

S2E5: Alex Jones & Alessandro DiSanto @ Hallow

Matt Castellini — Fri, 25 Jun 2021 15:32:13 -0500

Hallow is a Chicago-based startup building a Catholic prayer & meditation app to help you find peace, deepen your relationship with God, and sleep soundly every night.

Alex Jones is the CEO and Co-Founder and joined by his Co-Founder and Head of Growth & Finance Alessandro Disanto.

S2E4: Dan Knight @ Manifold Group on Early-Stage Due Diligence

Matt Castellini — Wed, 23 Jun 2021 08:36:08 -0500

Dan Knight is a Senior Associate at Manifold Group, a venture holding company based in Chicago. Dan has a background in software engineering and growth investing, and his experiences have provided him with a lot of information that he utilizes on a daily basis. This episode will be highly beneficial to anyone trying to enter into the field of venture capital or who will be pitching VCs in the future.

In this episode, we covered:

The Deal Memos
Quantifying ROI for SaaS Users
How to Analyze Top-Line Metrics
ARR Growth Rates
Types of Retention

And much more.... Please Enjoy!

You can Manifold Group on Linkedin, Twitter and their website & Dan on Linkedin.

S2E3: Trey Calver @ Michael Best on Term Sheets, Legalities of Early Stage Venture, Company Formation, Investing Overseas, & Resiliency in VC

Matt Castellini — Wed, 16 Jun 2021 18:57:41 -0500

In this episode, we covered:

Trey’s Passion for Entrepreneurship
Advice for Breaking into VC
Common Founder Legal Questions
Term Sheets
Challenges in Investing Overseas

Trey Calver is a Startup and Venture Attorney at Michael Best & Friedrich LLP, a full-service law firm. He started his career working for a venture capital business and a law company specializing in start-ups. He created and approved business and legal contracts for Motivate Venture Capital, including employee and contractor agreements, finance agreements, leases, term sheets, convertible notes, SAFEs, and warrants, among others. Concurrently, Trey worked as an attorney for a boutique start-up legal company that focused on the technology industry and services the specialized needs of start-ups and high-growth enterprises. He worked as an associate at NCT Ventures, an early-stage VC firm, for two years while getting his J.D. at The Ohio State University. Trey became an entrepreneur when he co-founded and helped scale High School AD Network, a bootstrapped online startup and communication platform for high school athletics teams, in 2017.

You can find Michael Best & Frierich LLP on their website, Twitter, and Linkedin, Trey on Linkedin, Venture Best’s Blog HERE, and Galen Mason on Twitter.

S2E2: Gabi Klapman @ Trvlpage

Matt Castellini — Fri, 11 Jun 2021 17:15:12 -0500

Trvlpage is a travel-based social media website and mobile app that makes it easy to log, share and plan trips with your network. Keep track of where you went, what you did, and how you enjoyed it using your Trvlpage, a map of the world with pins dropped in each place you've been.

Then, get your friends on board and easily search for recommendations from their Trvlpage when planning your next trips! Skip the endless searching, get trusted recommendations from your friends, family and like-minded travelers, and make your travel experiences best for you.

Season 2, Episode 1: Rick Desai @ Listen Ventures on Tiger Woods, Economics of Consumer Investing, Evolution of Value-Add Investing, & Content-Driven Commerce

Matt Castellini — Wed, 09 Jun 2021 00:00:00 -0500

In this episode, we covered:

Lessons Learned from Tiger Woods on Brand & Excellence
The Economics behind Consumer Investing
Brand vs. Branding
Value-Add Investing
The Future of Audio
Content-Driven Commerce

And much more.... Please Enjoy!

Rick Desai is the Head of Investments at Listen Ventures, an early-stage consumer-focused venture capital firm based in Chicago. Prior to joining Listen, he co-founded Dashfire, a Chicago-based startup studio that built and invested in over 40 businesses. His social entrepreneurial endeavors in urban Indian slums have earned him a Clinton fellowship. He began his career with Lehman Brothers in investment banking and Madison Dearborn Partners in private equity.

You can find Listen Ventures on their website, Twitter, Instagram, and Linkedin, Rick on Linkedin & Twitter, and Listen’s podcast- “Overheard: Where Venture Meets Culture” on Spotify & Apple Podcasts.

Restaurant Recommendation: Giant Restaurant

S1E20: Reno Perry @ Wiseful

Matt Castellini — Fri, 04 Jun 2021 13:26:38 -0500

Reno Perry is the CEO & Founder of wiseful, a career advancement platform where early & mid-career talent can book virtual calls with experts at top companies for 1:1 personalized career advice, interview prep, skills development, and powerful connections to land their dream job.

S1E19: Julia Ruge @ Sandalphon Capital On Evolution of Consumer Brands, Consumer Marketplaces, & Strong Sectors Of The Midwest

Matt Castellini — Wed, 02 Jun 2021 00:00:00 -0500

In this episode, we covered:

Key Attributes in Successful Founders
Indicators of Early-Stage Traction
Consumer Marketplaces
Future of Work and Healthcare post COVID-19

Julia Ruge is an Associate at Sandalphon Capital, a Chicago-based Venture Capital fund that invests opportunistically across the US but has a core focus on Chicago and the Midwest. She is involved with all areas of the fund at Sandalphon, including screening, due diligence, portfolio company support, and strategy. Prior to Sandalphon, Julia worked as an MBA Associate Intern at Corazon Capital while she completed the 1-year MBA program at Northwestern. Prior to business school, she worked at LAUNCH and Breakaway Ventures, where she specialized on building and executing technology-enabled consumer firms before joining Sandalphon Capital.

You can find Sandalphon Capital at their website & Twitter: @Sandalphoncap , Jon Ellis on his Twitter: @Jonrellis , and Midwest Tech Connect on Twitter: @Midwestdottech

Restaurant Recommendations: Spacca Napoli, Monteverde, and RL Chicago.

Manifold Group is a venture holding company based in Chicago with offices in Dallas, Los Angeles, and soon Atlantic Canada. Early stage private investments represent an extraordinary investment opportunity, but existing investment models in the space leave much to be desired. Manifold is a new model for growth in the new economy, designed to create and capture value at the early stage through synergies across its venture fund, incubation and acceleration studio, and advisory firm. Learn more about Manifold at https://www.manifold.group.

S1E18: John Nelson @ Vroom Delivery

Matt Castellini — Fri, 28 May 2021 13:41:40 -0500

John Nelson is the CEO & Founder of Vroom Delivery, the only eCommerce solution designed specifically for the $240B convenience store industry. Vroom’s cloud solution can be set up in just days, allowing for a quick and affordable roll-out of your own e-commerce program. Sell and market all of your products online — not just food — for home delivery, in-store pickup, curbside pickup, drive-thru and catering.

The accelerator John mentioned during our conversation, Blue Startups, is accepting applications until June 1. Apply for the chance to take your startup to the next level and spend four months in Hawaii!

S1E17: Guy Turner @ Hyde Park Venture Partners on State of Crypto, Investing Green Flags, CARR vs. ARR, & The VC-Founder Relationship

Matt Castellini — Wed, 26 May 2021 09:46:34 -0500

In this episode, we covered:

Investing in Pre-Launch Startups
Why Valuations Are Rising
Surprising Trends from 2020
Today’s Labor Market
CARR vs. ARR
HPVP’s Due Diligence Process
What Makes a Great Board Member

Guy Turner is a Managing Director at Hyde Park Venture Partners, an early-stage venture capital firm focused on high-growth, mid-continent technology startups. He has been with HPVP since its beginning in 2011. Prior to HPVP, Guy worked for the Boston Consulting Group where he concentrated on business strategy through a range of industries. He previously worked for Hyde Park Angels as an associate and an investor, and spent his early career as a mechanical engineer for Raytheon and General Electric. Guy has managed HPVP's investments in Fixer, MarketWagon, Upfront Healthcare, and Zipnosis, among others, and has led investments in a variety of tech firms.

You can find Guy on his Linkedin & Twitter and Hyde Park Ventures on their website and Linkedin.

Guy’s Blog & Personal Website: vcwithme

S1E16: David Pawlan @ Aloa

Matt Castellini — Fri, 21 May 2021 08:45:00 -0500

Aloa is a platform for outsourcing software development for startups. Aloa believes in a world where anyone can innovate freely, and currently, it sees software as a barrier to innovation. It has approached this space through a three-pronged method: Partner Network, Platform, & Strategist. Running a business is hard, software development shouldn't be.

The company is on the verge of launching its latest initiative, AloaPay, which will look to revolutionize the B2B invoicing process. The product will allow startups and enterprises to keep their papers organized, automate follow-ups, and help businesses avoid unnecessary fees.

S1E15: Steven Cook @ Chicago Ventures on API-First Companies, Alternative Asset Classes, & The Flywheel of Chicago Exits

Matt Castellini — Wed, 19 May 2021 00:00:00 -0500

Steven Cook is a Venture Associate at Chicago Ventures, a Chicago-based Venture Capital firm focused on the seed stage. Steven began his career in Venture Capital after playing professional basketball in Europe. He's a fantastic resource for advice on how to get your first job in Venture Capital and how to add value at the junior level.

In this episode, we covered:

Transitioning from professional basketball to Venture Capital
API first companies
Today’s alternative asset classes
The current enthusiasm around retail investing
The state of Chicago’s venture landscape

And much more... Please Enjoy!

S1E14: Cheryl Kemp @ Indifit

Matt Castellini — Fri, 14 May 2021 14:56:09 -0500

Cheryl Kemp is the founder & CEO of Indifit, the fitness entrepreneur's business management tool. Hundreds of IndiFit partners already benefit from technologies designed specifically for their business needs. IndiFit provides easy-to-use booking and business management resources to fitness and wellness instructors, allowing them to focus on the things that matter - cultivating and connecting with their audience.

You can find IndiFit at their website & Linkedin and Cheryl Kemp on Linkedin and her writing on her website.

S1E13: Ashley Hartman @ Bluestein Ventures on Product-Market Fit, Foodtech in Chicago, and Sustainable Unit Economics

Matt Castellini — Wed, 12 May 2021 00:00:00 -0500

Ashley Harman is the Senior Principal at Bluestein Ventures, a family office Venture Capital firm that focuses on investing in high-growth food and retail ventures. Prior to Bluestein, Ashley scaled a business across the country and spent time as an economic analyst at Nira during the height of the financial crisis.

In this episode, we covered:

The Parallels Between Economics & Venture
The Nature of Consumer Investing
Go-To-Market Strategies
The Velocity of Consumer Brands
Bluestein’s Recent Chicago Investments

And much more...

Ashley is actively involved in the Chicago community, where she serves on a number of boards and as a mentor at the Hatchery. She received her MBA from Harvard and attended Williams College for her undergraduate degree. She performs a variety of mission-critical tasks for Bluestein, including the screening and due diligence on new investment opportunities. She also assists the firm’s portfolio companies with their strategy formulation and execution.

You can find Ashley on her Linkedin and Bluestein Ventures on their website and Linkedin.

Chicago Restaurant Recommendations:

Podcast Recommendations:

Manifold Group is a venture holding company based in Chicago with offices in Dallas, Los Angeles, and soon Atlantic Canada. Early-stage private investments represent an extraordinary investment opportunity, but existing investment models in the space leave much to be desired. Manifold is a new model for growth in the new economy, designed to create and capture value at the early stage through synergies across its venture fund, incubation and acceleration studio, and advisory firm. Learn more about Manifold at https://www.manifold.group

S1E12: Brett Siegal @ Ruuster

Matt Castellini — Fri, 07 May 2021 00:00:00 -0500

Ruuster has brought together the info, tools, and people you need to plan for and execute your home purchase like a pro, even if it’s your first time.

Ruuster is a centralized app for the home buying process. As a home buyer, you can learn about each stage of the process, communicate with your agent via text and video, search properties, access property insights not available on Zillow, schedule tours, see a custom task list, share and sign documents, and acquire all of the vendors you need in one place, all on your phone.

With Ruuster, agents can qualify their leads, centralize their communication (text, images, videos, and documents) with all of their clients, send property recommendations, share and sign documents, maintain their schedule, and have one view of their pipeline all in their hands.

It's amazing that something like this doesn't exist, and it's also amazing that Ruuster is almost there with an initial version and first-to-market solution.

So far in its 10 months of launch, Ruuster has had thousands of users of the consumer platform. It has also partnered with world-class companies like Realtor.com, Better.com, New American Funding, and a number of top insurance companies.

Ruuster has opened up a distribution channel through agents, giving them the ability to integrate Ruuster into their current systems and provide their clients a branded homebuying app. And Ruuster developed an elegant suite of tools to help them prioritize their lead outreach and manage their pipelines.

S1E11: Jeff Cantalupo @ Listen Ventures on Consumer Investing in 2021, The Consumer Landscape in Chicago, and Building Brands at the Early-Stage

Matt Castellini — Wed, 05 May 2021 10:07:06 -0500

In this episode, we covered:

The Thesis Behind Listen Ventures
How Jeff Assess Early-Stage Brands
Investing in Calm, Factor_, and Catch Co.
"Glass Box Brands"
Consumer Investing in 2021
Chicago's place in Consumer Landscape

And much more.... Please Enjoy!

Prior to founding Listen, Jeff spent 10 years in the advertising industry at Leo Burnett where he helped large brands innovate and craft their brand story.

Since founding Listen, Jeff has invested in over 20 startups. He looks to provide branding and business strategy for consumer-focused early-stage companies. Jeff invested in one of the most successful consumer tech companies in the past ten years in Calm, and he has an impressive roster of Chicago-based investments including Factor, and Catch Co.

You can find Listen Ventures on their website and Linkedin and Jeff on the podcast- “Overheard: Where Venture Meets Culture” on Spotify & Apple Podcasts.

Chicago Restaurant Recommendations: Momotaro, Cruz Blanca, and Gene & Jude’s.

S1E10: Jackie DiMonte @ Chicago Ventures on Maturation of Chicago VC, Seed Investing in 2020, & Impending Series A Crunch

Matt Castellini — Wed, 28 Apr 2021 00:00:00 -0500

Jackie DiMonte is a Partner at Chicago Ventures, an early-stage Venture Capital firm based in Chicago. She began her career at Accenture as a consultant. She then worked for an IoT startup named Silver Spring Networks while receiving her MBA at The University of Chicago Booth School of Business. Jackie entered Venture Capital at Hyde Park Venture Partners prior to becoming a Partner at Chicago Ventures.

In this episode, we cover:

The maturation of Venture Capital in Chicago
A recap of seed investing in 2020
Prognosis for seed investing in 2021
The impending Series A crunch
NFT's

You can find Jackie on LinkedIn & on Twitter and Chicago Ventures at their website.

Resources discussed:

Jackie’s newsletter Day by Jay,
Seeding the Exception article
Her NFT - Floating Houses.

zg1LRLBZYzJ5XvU2fuwJ

S1E9: Lance Dietz @ KB Partners on Lessons from the Military, Sports Tech Investing, and Chicago's Place in Sports Tech

Matt Castellini — Wed, 21 Apr 2021 00:00:00 -0500

Lance Dietz is a Principal at KB Partners, a Chicago based investment firm that focuses on early stage venture capital investments in the Sports Technology Industry. Prior to KB, Lance attended West Point for his undergrad where he played Division one basketball. After graduating, Lance served in the US Army as an engineer officer, was deployed in Afghanistan, and thereafter received an MBA from the University of Chicago Booth School of Business.

Once Lance graduated from Booth, he began in investment banking at JP Morgan. He spent time in the M&A group. In 2018, Lance joined KB Partners where he now leads due diligence and sourcing for early stage startups in the Sports Tech space.

In this episode, we covered

Lessons Lance took from his time in the military
The nuances of Sports Tech investing
The thesis behind KB Partners
The maturity and state of the Sports Tech industry
Chicago's place in the Sports Tech scene

Please Enjoy!

You can connect with Lance via Linkedin or Twitter and KB Partners on Twitter, Linkedin, and their website.

Organizations & Reading recommendations from Lance:

S1E8: Colin Keeley on Micro-PE, Future of Audio, How Chicago can Improve, and Leveraging Human Capital

Matt Castellini — Wed, 14 Apr 2021 00:00:00 -0500

Colin Keeley is the co-founder and operator of a number of companies, including Avocado, Formulated, and now Blinksale. After college, Colin worked as a Product Manager & Marketing Manager at Luma.Tv and then ran Geneva Denim for a stretch before heading to business school at the University of Chicago. During business school, Colin launched Bevy, a sharing economy startup that allowed customers to rent anything. He also launched The Tech In Chicago Podcast, the first Chicago-focused early-stage podcast.

Matt caught up with Colin Keeley to discuss his latest entrepreneurial endeavors, Avocado and Formulated. They also discussed the process of starting a podcast, his plans for scaling his Micro-PE model, and the flywheel effect of big exits in Chicago.

Key Takeaways

Micro-PE has a boringness discount. All these startups that grow super fast, they're super sexy. But, you can actually buy product-market fit and recurring revenue for a pretty low multiple, if it isn't one of these sexy startups in a sexy space. There is an opportunity around the $100-200K MRR range, where a single developer has built something that has real product-market fit, hundreds of customers, but they don't really have that skill-set to take it to the next level. They don't have the skillset to put the processes in place or any real best practices for sales and marketing.
Audio courses are designed for a clear return on investment. They take you from A to Z in learning. You could get the same knowledge from podcasts, but you spend a lot more time doing that. People sell audio courses for that ROI and to get consumers from A to Z. Podcasts are driven by advertisements. Joe Rogan is incentivized to have a three-hour podcast so he can fit in an hour of ads.
Chicago needs bigger exits. It’s a flywheel - we need more people that have good outcomes that come back and become angel investors. It’s progressing. We took a few steps back during COVID, but Chicago has a lot going for it.

Please Enjoy!

Colin’s Social, Podcasts, and Companies:

Podcast recommendations from Colin:

Chicago Food Recommendations:

Manifold Group is a venture holding company based in Chicago with offices in Dallas, Los Angeles, and soon Atlantic Canada. Early stage private investments represent an extraordinary investment opportunity, but existing investment models in the space leave much to be desired. Manifold is a new model for growth in the new economy, designed to create and capture value at the early stage through synergies across its venture fund, incubation and acceleration studio, and advisory firm. Learn more about Manifold at https://www.manifold.group.

S1E7: Cristin Pacifico @ TechNexus on Early-Stage Operating, Chicago vs. Silicon Valley, Outdoor Recreation Startups, and Paths to Venture

Matt Castellini — Wed, 07 Apr 2021 10:03:41 -0500

Cristin Pacifico is a Manager at TechNexus Venture Collaborative, a Venture Collaborative that combines businesses, corporate joint-ventures, private equity funds, and a startup investment portfolio. Given the fund structure at TechNexus, Cristin spends a large amount of her time strategically thinking about how startups and large corporations can work together and find synergies. She focuses on Direct-to-consumer and e-commerce business, marine and outdoor recreation, and diversity, inclusion, & impact investing.

Prior to TechNexus, Cristin worked in a variety of operating and investing roles. She was an early employee at Home Chef, where she worked on the finance team and was able to help steer the company through its merger with Kroger. Before her time at Home Chef, she started out as an investment banker at Robert W. Baird. She worked primarily on the sell-side M&A team with industrial companies, similar to some of the corporate partners that she now works with today at TechNexus.

Cristin graduated from Notre Dame and during her time there, she co-founded a microlending-non profit called JIFFI, which she still serves on the board of today.

Cristin spoke with Matt about the Chicago investing ecosystem, her experience at HomeChef, the exciting verticals she’s seeing in the outdoor & recreation industry, and other 2021 trends.

Please Enjoy!

You can find Cristin on LinkedIn & on Twitter and TechNexus Venture Collaborative on their website.

Cristin’s article on

Reading Recommendations:

Chicago Restaurant Recommendations: Nonnina Chicago, Siena Tavern, & Fertido.

S1E6: Mark Achler @ MATH Venture Partners on His Entrepreneurial Journey, B2B Customer Acquisition, & Chicago VC

Matt Castellini — Wed, 31 Mar 2021 00:00:00 -0500

Mark Achler is the Co-Founder and Managing Director of Chicago-based MATH Venture Partners. Previously, Mark drove innovation and sales at Redbox and co-founded a number of successful startups in his career. He began his VC career in the Chicagoland area at Kettle Partners. He then co-founded MATH Venture Partners in 2014, which invests in early-stage technology businesses, such as Chowly, Acorns, and Built In.

Mark spoke with Matt about his background, what led him into Venture Capital, the genesis of Math Venture Partners, why doing your homework is so important, and the history of the Chicago startup ecosystem.

S1E5: Jackson Bubala @ Motivate Venture Capital on B2B Marketplaces, E-Commerce SaaS Investing, Food Delivery, & How the Chicago VC Ecosystem Can Continue To Improve

Matt Castellini — Wed, 17 Mar 2021 00:00:00 -0500

Jackson Bubala is a Senior Associate at Motivate Venture Capital, a Chicago-based early-stage fund. He recently joined the Motivate team after spending the first three years of his career at Manifold Group. He writes a weekly newsletter, Stealing Signs.

Jackson spoke with Matt about his background, why he has enjoyed working at generalist funds, the biggest opportunities in e-commerce, why B2B marketplaces excite him, and the Chicago Food Scene.

S1E4: David Rabie @ Tovala On Recent Series C, Staying Lean As A FoodTech Startup, And Why Tovala Chose Chicago over Silicon Valley

Matt Castellini — Wed, 10 Mar 2021 00:00:00 -0600

David Rabie is the co-founder and CEO of Tovala, a FoodTech service built for the busiest people. Based in Chicago, Tovala prepares and delivers fresh meals that can be cooked to perfection in its proprietary oven.

David grew up in Southern California and moved to Chicago in 2013 to attain his MBA from the University of Chicago Booth School of Business. While completing his MBA, David realized that he wanted to solve the modern professional’s problem of cooking a convenient, healthy, and quick home meal. Since then, Tovala has clearly achieved product-market fit and successfully scaled to a growth-stage company. Tovala grew its revenue by 10x in the last year and a half and has surpassed 3 million meals shipped nationwide. The company has also successfully raised multiple rounds of financing, including a recent $30 million series C investment.

David spoke with Matt about the background of Tovala, their early growth challenges, how his leadership role has changed, and why he chose Chicago over Silicon Valley.

Please Enjoy

S1E3: Joe Dwyer @ Manifold Group on Serial Entrepreneurship, the State of Venture Capital, Innovating VC, and Crypto in Chicago

Matt Castellini — Wed, 03 Mar 2021 00:05:00 -0600

Joe Dwyer is a Founding Partner at Manifold Group (FKA Founder Equity & Digital Intent). Manifold Group is a venture holding company based in Chicago. Prior to Manifold Group, Joe worked in early-stage venture capital here in Chicago, but Joe is a serial entrepreneur at heart. He has over 25 years of experience creating and growing new businesses.

Joe spoke with Matt about his background, the startups that he founded, his philosophy surrounding Entrepreneurship, and the state of Venture Capital. They dig into Joe’s passion for early-stage companies, the re-branding of Manifold Group and Manifold Ventures, and the dramatic changes he’s seen in Chicago’s Venture Capital landscape. Finally, Joe provides listeners with his current views on Crypto.

S1E2: Austin Ju @ New Stack on Networking, Growth Marketing, and the State of Venture Capital Podcasts

Matt Castellini — Wed, 03 Mar 2021 00:03:00 -0600

Austin Ju is a Deal Lead at New Stack Ventures, a Venture Capital firm based in Chicago that leads rounds at the pre-seed through seed stage and “Invests in the Exceptions.'' Prior to New Stack, Austin spent 2 years at CoEfficient Labs where he helped early-stage startups nail their customer acquisition and top-line growth metrics through paid acquisition and product optimization.

Austin spoke with Matt about how he got into Venture Capital, The Full Ratchet, the state of VC podcasts, and how he transitioned from marketing to investing. They discuss New Stack’s investment thesis, investing through the pandemic, their due diligence process, and one of their most recent successful investments, Tovala.

Season 1, Episode 1: Sara Taylor-Demos @ Cora Home on Building a B2B Marketplace, Customer Discovery, Pivoting, & the Interior Design Industry

Matt Castellini — Wed, 03 Mar 2021 00:00:00 -0600

Sara Taylor Demos is the founder and CEO of Cora Home, the first data-driven SaaS platform and product marketplace for furnishing. Founded four years ago, Cora is based in Chicago and is building a two-sided SaaS enabled marketplace for the $77 billion B2B furnishing industry. Cora allows vendors and designers to manage their teams, their trade accounts, and their communications in a digital and streamlined way.

Sara spoke with Matt about her background, the furnishing industry, pivoting, why she decided to incorporate in Chicago, and resources that have helped guide her on the journey.

Welcome to Chicago Capital

Matt Castellini — Sat, 27 Feb 2021 16:05:21 -0600