The confession: he got the predictions right and the timelines wrong. Fifteen years bullish on driverless cars, and we are still not there. In his words, "I've been really right in my predictions, but not as good in my timeline of predictions."

The cost: not money, time. He kept underestimating how hard people resist a change that is better for them. The ATM card, online banking, telemedicine. Every one arrived years after it should have, and the delay was human, not technical.

The insight that reframes the rest: disruption does not find you when you are weak. It finds you at your peak. Kodak was one of the two most recognized brands on earth when digital photography hit. The music industry's best year ever was 1999, and then Napster came.

The takeaway: stay out of the bubble. The financial press, the business school stage, the celebrity of being a CEO. That is where you lose track of who your customers actually are, and that is where the disruptor finds room.

Jeff's book, Disrupters at the Gate: https://www.simonandschuster.com/books/Disrupters-at-the-Gate/Jeffrey-Cole/9781646872909

Center for the Digital Future: https://www.digitalcenter.org

Find me: https://www.linkedin.com/in/jaminbrazil/
Listen and follow: https://pod.link/6798471198

The confession: he built a pure software company for a market that wanted service, and he wasn't the operator his own business needed once it passed twenty people.

The cost: he found out standing in a hallway at Procter & Gamble. A client raved about the project, so he asked what was coming next. "Oh no, we've got everything we need for years now." A competitor that embraced being a tech-enabled service instead took off. His own exit, in his words, balanced itself out, but he can see the more lucrative outcome he didn't take.

The takeaway: the two-hour workday. You get about two hours of peak executive function. Put the most important thing there, shield it, and even if you only get one of the two hours, you've won the day. Everything else is negotiable.

The question for your team this week, his: does everybody know what their most important thing is, and does it map to the most important thing for the company?

Steve on LinkedIn: https://www.linkedin.com/in/steve-august-b2b-adhd-business-founder-coach/

ADHD Entrepreneur Accelerator: https://adhd-accelerator.com

Find me: https://www.linkedin.com/in/jaminbrazil/
Listen and follow: https://pod.link/6798471198

The confession: he has always overestimated how fast customers will change their behavior, and underestimated how long it takes.

The cost: value propositions with unarguable economics that went nowhere. The same wall showed up again at Flashpoint, twenty-five years later, when a client team loved the work and still couldn't sell it upstairs because leadership wanted crosstabs.

The takeaway: ask it one person at a time, never in a group. If we had $100 million in funding, what would we be investing in right now that is going to bite us when we don't? Push past the first answer.

Stephen on LinkedIn: https://www.linkedin.com/in/stevemugford/
Flashpoint.AI: https://www.flashpoint.ai/
Find me: https://www.linkedin.com/in/jaminbrazil/
Listen and follow: https://pod.link/6798471198

Rob followed the playbook for two years. Customer interviews, discovery research, all of it. Nothing worked. Then his company took off for reasons he couldn't explain, going from zero to a few million in revenue in two years, and he's been reverse-engineering why ever since.

The confession: when customers started closing fast, thousands of dollars after a single sales call, he read it as product-market fit and poured on the gas. He wasn't looking at retention. And because he was selling annual contracts, the earliest he could have found out whether he was right was eleven and a half months later.

The cost: he got lucky. A second product landed and bought the company another year. He's watched friends' startups post entire quarters at zero percent retention after their Series A.

The takeaway: stop measuring time to value, because a customer can get real value from you and still leave. Measure time to not going to churn. And go back to the last customer who bought strangely fast, then listen to what they said in the first few minutes about why they were talking to you that day.

Rob on LinkedIn: https://www.linkedin.com/in/rsnyder1/

The Power of Pull: https://a.co/d/0ildfsrD

Find me: https://www.linkedin.com/in/jaminbrazil/

Listen and follow: https://pod.link/6798471198

Before the bestseller lists and keynotes in 32 countries, Rohit spent 15 years leading marketing strategy at Ogilvy and Leo Burnett. In this episode he breaks down the SIFT method behind his upcoming CRC keynote, explains why he killed a trend report that was still working after ten straight editions, and gets honest about the part of the journey that didn't go to plan.

The confession: At the agency, the side gig of speaking on stage grew into something his day job couldn't hold. He did the honest thing and went to his bosses to offer a split of the fees. They told him the holding company's accounting made that impossible, and to just take a day off for each gig and keep the money instead. What nobody accounted for is that the big events book three to ten months out. He locked in a date, the date landed on top of a $20 million pitch, and the question stopped being whether he was moonlighting and became whether he was working for them at all.

The cost: It cost him his job. He also thinks it cost him time he could have spent building his own business earlier. He is careful about the regret, though. He wouldn't change the timing, only the empathy he showed the colleagues who picked up his slack.

The takeaway: Change the question. Insights work almost always points at what to build next, so ask the opposite instead. Based on this data, what current product should we kill? What is already dying in two years whether we act or not? Same data, different insight. And a habit for outside the data: pick up a magazine that isn't for you, and read the advertising as closely as the articles, because the ads tell you who that audience actually listens to.

Rohit is keynoting "How To Be A Non-Obvious Thinker (And See What Others Miss)" at the Insights Association's Corporate Researchers Conference, September 15–17 in Chicago. Grab your ticket: [jamins-ia tracked link, confirm before publish]
CRC: https://www.insightsassociation.org/Events/CRC-September-15-17-Chicago

Get the book: Non-Obvious Thinking:
https://www.amazon.com/dp/1646871618?lv=shuf&channelId=500&plpRedirect=mhFallbackHis

Non-Obvious Substack: https://nonobvious.substack.com/

The trend scorecard he mentions: https://nonobvious.com (trends section)

Connect with Rohit: https://www.linkedin.com/in/rohitbhargava/ 

Find me: https://www.linkedin.com/in/jaminbrazil/

Listen and follow: https://pod.link/6798471198

Along the way Jenny founded Own Your Career, one of Google's largest internal career-development programs, built as a side project while she held a full operations role. In this episode she gets into the three fears that stop people from acting, the difference between a truth and a tale, and the moment on a Boulder road at night when she realized something had to give.

The confession: She wanted Wild Courage to be a New York Times bestseller badly enough that she went full tilt for the year to eighteen months around the launch and couldn't see past it. It worked. She still says the juice probably wasn't worth the squeeze, because of what the obsession took from her family.

The cost: Her son was waiting in the car while she finished one last email, one last piece of book marketing, always one last thing. He got out, came back into the house, and told her why he didn't think she was coming: "Mom, because all you ever do is work." She calls it a dagger, and it's the thing that made her ask whether she was actually voting with her calendar. Two days later he dragged a friend into her office to show off the book cover, proud of her. Both things were true at once.

The takeaway: Stop opening with the spreadsheet. Use GRAB on your first slide when you need a decision from a stakeholder. Goal, Request, Action, Benefit. The ask belongs at the top, not on slide forty, so nobody spends thirty minutes wondering whether you want budget, a decision, or a shoulder to cry on.

Jenny is speaking on "Wild Courage: The Confidence to Act Before You Have All the Answers" at the Insights Association's Corporate Researchers Conference, September 15 through 17 in Chicago. Her session is Wednesday the 16th, 9:10 AM CT.

CRC: https://www.insightsassociation.org/Events/CRC-September-15-17-Chicago

Connect with Jenny: https://www.linkedin.com/in/jennyilles/

Get the book: https://wildcouragebook.com/

Find me: https://www.linkedin.com/in/jaminbrazil/

Listen and follow: https://pod.link/6798471198

Joe was an early leader at Contently, where the inbound engine his team built drove over 90% of revenue as they scaled to 50 million in annual sales. His newsletter on storytelling and AI reaches nearly 200,000 subscribers, and his workshops have helped Marriott, Chase, Caseware, and Dell put their own storytelling to work.

The confession: As Contently scaled and he was getting pulled into strategy and client work, he couldn't let go of the small things. Copy editing the print magazine so there'd be no typos. Reviewing newsletter subject lines before they went out. Meanwhile he'd be in three hours of back-to-back meetings, holding his own team up.

The cost: His team's trust, autonomy, and growth. He calls helping your team grow the highest responsibility a leader has, higher than the results you report to the board. He found out from direct feedback, including his longtime editor Jordan telling him plainly: you made me editor-in-chief, let me be editor-in-chief.

The takeaway: Open hot. Dr. Paul Zak's research on the neuroscience of storytelling says people don't have short attention spans so much as short consideration spans, so get into a narrative that exemplifies your data within the first fifteen seconds instead of winding up to it. Then stop letting good research die in the darkness. Chop it into pieces that speak the grammar of the channel you're publishing on.

Joe's Substack, The Storytelling Edge: https://storytellingedge.substack.com/

Joe is running a hands-on workshop at the Insights Association's Corporate Researchers Conference, September 15 through 17 in Chicago, on why storytelling is the superpower of the AI age. Grab your ticket: bit.ly/jamins-crc26

Connect with Joe: https://www.linkedin.com/in/joe-lazer/
Listen and follow: bit.ly/jamins-lazer
Find me: https://www.linkedin.com/in/jaminbrazil/

Over nearly four decades at Publicis, across two eras and a dozen companies, Rishad helped the world's biggest brands navigate change from the inside. In this episode he lays out the five tectonic shifts reshaping business, three reasons leaders get the technology question wrong, and why companies don't transform, people do.

The confession: The biggest mistake he and his team made scaling Publicis was pouring their energy into the fast parts of change, strategy, M&A, and reorganization, and not leaving enough time for the people part. It's easy to do a reorg. It's hard to bring people along, and that's the part that actually determines whether anything changes.

The cost: Get the people part wrong and you can lose market share, sometimes the whole company. You lose world-class talent before you fix it. And your credibility as a leader can get damaged past the point of being taken seriously anywhere else.

The takeaway: Block one hour a day to learn, and steal it from your work hours, not your family or your sleep, because when the leader stops learning, the company stops transforming. Then, every so often, put your team on the opposite case: if you had to destroy your own company, how would you do it? It's the fastest way to see how to build it.

Ask Rishad's writing directly, free, no ads, no signup: https://rishad.ai
His newsletter, The Future Does Not Fit in the Containers of the Past: https://rishad.substack.com

Rishad is speaking on "How to Thrive in Tectonic Times" at the Insights Association's Corporate Researchers Conference, September 15 through 17 in Chicago. Grab your ticket: bit.ly/jamins-crc26

Connect with Rishad: https://www.linkedin.com/in/rishadtobaccowala/
Listen and follow: bit.ly/jamins-rishad
The 2:1 Test: Did you fund the decision and starve the landing? https://bit.ly/jamins-test21
Insights Assocication's CRC Event: https://www.insightsassociation.org/Events/CRC-September-15-17-Chicago

Kristin has spent two decades building and selling research companies, and now sits on the other side of the table advising the founders coming up behind her. In this episode she gets specific about what it costs to be the person who can't stop doing everything, and what to ask your team when you finally decide to stop.

The confession: You make more than twenty-five dollars an hour. Why are you cleaning the bathroom?

The cost: Sleep, stress, sanity. The bill comes due in the things you stop noticing.

The takeaway: Ask every person on your team how they specifically contribute to the success of the business, or how they help it grow. The answers tell you who understands their job and who is just doing tasks.

Kristin and I co-led a CEO coaching cohort together for three years, so this one is a conversation between people who already know each other's scar tissue.

Connect with Kristin: https://www.linkedin.com/in/kristinluck/
Listen and follow: bit.ly/jamins-luck

Every episode is one guest, one confession, and one thing you can use Monday morning. No highlight reels, no frameworks invented after the fact. Just the part where it went sideways and what it cost.

Hosted by Jamin Brazil, 3x founder with 4 exits, who's sat in the founder seat, the CEO seat, and the COO seat.

First episodes drop August 18.