Not Another CEO Podcast

He rejected a founder’s seed round. When that founder went out to raise his Series A, Jake’s firm was the first call he made.Jake is the Managing Partner at Camber Creek, a venture firm that invests in proptech and fintech, has nearly $1 billion under management and has backed more than 50 companies, including Bilt Rewards. Before venture, he worked in consulting at Deloitte and BCG, then in government, first at GSA and then as a senior policy advisor on the National Economic Council in the Obama White House.He and David have known each other for over 25 years. In this episode of Not Another CEO, he explains how he decides whether to back a founder, what founders get wrong about his side of the table, and what the White House taught him about building companies.Here are the best takeaways from the episode:1. Resilience beats everything: Jake backs founders who found a problem with no good solution and will do whatever it takes to solve it, not people drawn to the Silicon Valley or YC image. Very few companies become multibillion dollar successes overnight, so he wants the founder who can keep going through the hard stretches.2. A no can be a request for proof: Jake passed on Bilt’s seed round but told the founder to stay in touch. Over the next 12 months the founder did what he said he would, including partnerships with banks, airlines and hotels, and Camber Creek was the first call for the next round.3. Self-awareness is a filter: Jake would rather hear what you got wrong than hear that everything is perfect. A founder who can’t name what keeps them up at night is a quick pass, because it shows a lack of self-awareness and empathy for customers, employees and investors.4. He decides fast, then verifies: About 30 minutes tells Jake whether he wants to partner with someone for ten years. Customers, other investors and even a college roommate then tell him whether that person will build a big company.5. Bring your board questions you can’t answer yourself: The most common pitfall Jake sees is founders asking questions they already know the answer to. Send the financials in advance and spend the meeting on real strategic choices, with board members who bring different backgrounds.Quote of the Show“To me, one of the biggest turn offs is when I meet a founder and I say, you know, what keeps you up at night? And they say nothing.” - Jake Fingert, Managing Partner, Camber CreekGuest featured in this episode: Jake Fingert, Managing Partner, Camber CreekLinkedIn: https://www.linkedin.com/in/jake-broder-fingert-a4388b3/Camber Creek: https://cambercreek.com/We also break this episode down into a full write-up on Substack, where we turn every conversation into a practical playbook with the biggest lessons, frameworks, and strategies discussed in each episode.Chapters:00:00 Introduction02:07 The one trait Jake looks for in founders03:53 Passing on Bilt's seed round08:23 The red flag: "nothing keeps me up at night"10:21 How fast a VC decides15:25 How to run a board meeting22:53 From GSA to the White House27:23 What founders don't understand about VCs33:13 How Jake has changed in ten years38:00 Is this 2021 again?42:53 Moats and founder-led sales in the AI era55:15 What to teach your kids: AI tools and finding truth

Big funds may not fight for you unless you’re in their top 5% of companies, and Michal Rokosz explains how to tell which kind of investor you’re talking to.Michal is a partner at Inovo Venture Partners, a Warsaw-based seed fund and one of the leading early-stage investors in Central and Eastern Europe. Before investing he was an operator, as managing director at foodpanda and COO at Booksy, and he has backed more than 25 companies.In this conversation with David Politis, he breaks down how fast VCs decide, why capital can beat operational excellence, and how his region went from copying proven startups to building frontier AI companies.Key takeaways1. Investors decide faster than you think: Michal can often tell within the first five minutes whether a founder is an outlier, and the full decision takes about two weeks. His fund found that its fastest investments tended to perform best.2. Your backstory is part of the pitch: From an Olympiad win to an overnight drive for a missing part, the stories founders skip are often what set them apart. Michal says a founder who can’t explain why they’re exceptional will lose to one who can.3. More money can beat better operations: At foodpanda, his team was less efficient than several competitors but had more funding, and that was enough to win. In AI, the same logic means a company that grabs the market while losing money can beat one that gets the economics right first.4. A VC isn’t grading your business: Michal says his job is to find the anomalies. A fund needs one or two companies to return the whole fund, so a founder with a lower ceiling shouldn’t expect the same valuation as one with a higher ceiling.5. Big funds may not fight for you: Outside a large fund’s top 5% of companies, you may get little attention, while a smaller fund may treat you as one of its most important bets. Talk to a few of an investor’s founders before you sign.6. Not every founder should raise venture capital: Michal argues that some founders are better off bootstrapping to a profitable business, and that VC only makes sense if you’re aiming to build something huge.Quote of the Show :“If I have like five times more money and I'm 20% less efficient, I'm still going to win” - Michal Rokosz, Partner at Inovo Venture PartnersGuest Featured in this Episode: Michal Rokosz, Partner at Inovo Venture PartnersLinkedIn : https://www.linkedin.com/in/mrokosz/Inovo Venture Partners : https://www.linkedin.com/company/inovovc/home/We also break this episode down into a full write-up on Substack, where we turn every conversation into a practical playbook with the biggest lessons, frameworks, and strategies discussed in each episode.Chapters:00:00 Meet Michal Rokosz02:07 What Inovo looks for in a founder04:07 Why your backstory is the pitch09:23 How fast Inovo decides to invest11:10 Viktor and the founder who killed his own project16:40 Why big VCs won't fight for you19:56 How Central and Eastern Europe has changed28:00 Are we in an AI bubble?31:21 Why VCs need a company that can return the fund36:21 Two founders, one wins by losing money41:15 What founders get wrong about VCs43:04 Why Michal loves being an investor

When you sell your company and hit the milestone most founders only dream of, why does it feel so lonely?Barak Kaufman has met around 2,000 exited founders, and almost all of them describe the same thing.In this episode of Not Another CEO Podcast, I sat down with Barak Kaufman, an investor, operator, exited founder and community builder.Barak started his career at Insight Partners, co-founded Intello (Which competed with my company, BetterCloud), and sold it to SailPoint in 2021. He then started Post-Exit Founders, now more than 7,000 members across 12 countries. Today he is a partner at Vine Ventures and Chief Strategy Officer at Wonderful, an applied AI company.We cover identity loss after an exit, building in the AI era, startup life in New York and Israel, and what founders get wrong about investors.Takeaways1. The hardest part of an exit is identity, not money: Barak says most exited founders feel lost and lonely, and many end up with a boss for the first time in years.2. Take a year off and commit to nothing: His advice is 12 months, not six and not 24. The biggest mistake he sees is jumping into the next company because the in-between phase is uncomfortable.3. Luck and agency both matter: Exited founders split on whether they got lucky or slaved for it. Barak believes in agency and says the founders he respects most don’t blame the situation.4. Building in the AI era is faster, but the fundamentals haven’t changed: Wonderful’s deals are mostly over $1M a year, versus about $30K at Intello. A-plus talent, enablement and enterprise trust still decide who wins.5. Believe your pitch: Barak admits he’s not sure he truly believed his own billion-dollar story at Intello. His standard for founders is believing that you will get there, not that you can.6. Run your fundraise like a process: Most VCs have less figured out than founders think, and FOMO drives a lot of decisions. Be tactical, not passive.Quote of the Show“When you build a company and you sell that company and you reach the milestone that many would only dream of, it ends up feeling very weird and very lonely.” - Barak Kaufman, Chief Strategy Officer, WonderfulGuest Featured in this Episode: Barak Kaufman, Chief Strategy Officer, WonderfulLinkedIn: https://www.linkedin.com/in/barakk/Post-Exit Founders: https://pef.co/Vine Ventures: https://vineventures.com/Wonderful: https://www.wonderful.ai/We also break this episode down into a full write-up on Substack, where we turn every conversation into a practical playbook with the biggest lessons, frameworks, and strategies discussed in each episode.Chapters:00:00 Trailer & Introduction02:47 From investor to founder to Wonderful's Chief Strategy Officer04:46 What Wonderful does and how it started07:37 Building in the SaaS era vs. the AI era11:07 What stays the same: talent, enablement and enterprise sales17:44 Inside Post-Exit Founders: the identity loss after an exit22:30 Take a year off, and the paths after an exit30:28 Why everyone wants to be a founder34:06 Luck, skill and what sets exited founders apart38:05 Agency over timing: Airtable, Miro and COVID44:29 New York vs. Israel startup ecosystems48:01 Inside Israel's talent war51:14 What founders don't understand about investors57:53 FOMO, hot rounds and the flight to quality1:00:02 The advice he'd give his younger self

Most founders think the best story wins. Alex Konrad has spent 15 years watching what happens when the story is all there is.In this episode, Alex Konrad, Founder of Upstarts Media, joins me to share what he's learned from covering the biggest names in tech. He spent more than a decade at Forbes writing cover stories on people like Marc Benioff and the Collison brothers, ran the Midas List for ten years, and co-created the Cloud 100. In February 2025, he left to build Upstarts Media on his own.From the one trait he sees in the most successful founders to why great storytelling can make or break a company, Alex unpacks what he's learned from watching thousands of founders and investors up close. We also get into the loneliness of being a solo founder, the customer stories that stay with you, and what it takes to build a bootstrapped media company.If you're building a company, raising capital, or wondering whether you're built for the founder journey, this conversation will change how you think about obsession, storytelling, and what actually lasts.Key Takeaways:- The Obsession Is the Real Qualifier: The most successful founders Alex has interviewed aren't building for wealth or Twitter popularity. They're almost sick in the head about the work, and they couldn't live with themselves doing anything else. Alex explains why the founders chasing the lifestyle, the YC badge, or the title tend to burn out faster.- Find Your One Superpower: Early on, a founder should be able to do one thing better than anyone they could hire. For Alex, it's storytelling. For me, it turned out to be motivating people.- Storytelling Should Accelerate the Story, Not Be the Story: If you're a great salesperson selling magic beans, it catches up to you eventually.- What Great Investors Actually Do: After a decade on the Midas List, Alex says the number one thing CEOs want is an investor who feels like part of the team.- Great Founders Find Great Markets: Silicon Valley says a great founder can't fix a bad market. Alex isn't so sure. With how many companies pivot in the AI era, he believes a great founder will evolve into the market, or prove everyone wrong about how big it was.- Online Can Build a Brand or Eat Your Day: Alex recently wrote about CEOs and investors who are highly online to terminally online. We talk about the real advantage of a public brand, the risk of the doom scroll, and why he suggests putting your time on social media on the calendar.Quote of the Show:"Storytelling should accelerate your story, for good and bad. It shouldn't be the entire story." – Alex Konrad, Founder, Upstarts MediaGuest Featured in This Episode: Alex Konrad, Founder, Upstarts MediaLinkedIn: https://www.linkedin.com/in/alexrkonrad/Upstarts Media: https://www.linkedin.com/company/upstarts-media/We also break this episode down into a full write-up on Substack, where we turn every conversation into a practical playbook with the biggest lessons, frameworks, and strategies discussed in each episode.Chapters:00:00 - Intro02:01 - How Alex decides who to cover11:37 - Why Alex left Forbes to build Upstarts17:52 - The number one trait of successful founders19:56 - Founder cycles and finding your one superpower27:05 - The Midas List and what makes a great investor34:35 - Storytelling and the trillion-dollar outcome40:23 - Building Upstarts solo and bootstrapped42:14 - The loneliness of being a solo founder44:26 - Crazy customer stories and "Elon-level" security49:16 - Terminally online founders54:59 - Where Upstarts is in three years

Eoin Hinchy spent 15 years living the exact problem he'd eventually build a company to solve. First at Deloitte, then eBay, then as Director of Information Security at DocuSign, he watched security teams burn hours gluing broken tools together by hand. So in 2018, he and his co-founder Thomas left to build the product they wished they'd had, out of a small office in Dublin.That company is Tines. Today it's 450 people across Dublin, Boston, San Francisco and Sydney, has raised over $270 million from Goldman Sachs, SoftBank, Accel and others, is valued at over a billion dollars, and is approaching $100 million in ARR. In this episode, we talk about the moment Tines decided to blow up its own winning product to get ahead of AI, why he's never built a pitch deck in his life, and the piece of advice he'd give himself before his very first job.Key Takeaways:Why founders beat sales teams from $60B companies: Eoin explains the difference between a missionary and a mercenary, and why buyers can feel it immediately.Refounding the company at its best quarter ever: The "falling off a building" analogy Eoin uses for why Tines rebuilt its core product around AI before the market forced their hand, and how he broke the news to his team and board.Why no customer was ever forced to migrate: The promise Eoin made to protect the people who got Tines to where it is today.Raising $270M without a single pitch deck: How Tines picked investors the way you'd pick a co-founder, and why Eoin never went looking for capital."Nobody cares" : The reframe that Eoin says makes the hardest parts of the job easier, not harder.The Wizard of Oz moment: What happened the first time Eoin worked inside a company he used to think was run by geniuses.Quote of the Show:"The failures aren't going to be these dramatic explosions. They're going to be this kind of like quiet, unrequited effort where you put in all this hard work and like, everybody's kind of like, yeah, cool and moves on."— Eoin Hinchy, Co-Founder & CEO, TinesGuest Featured in This Episode: Eoin Hinchy, Co-Founder & CEO, TinesLinkedIn: https://www.linkedin.com/in/eoinhinchy/Tines: https://www.tines.com/We also break this episode down into a full write-up on Substack, where we turn every conversation into a practical playbook with the biggest lessons, frameworks, and strategies discussed in each episode.Chapters:00:00:00 - Introduction00:02:35 - Best Decision at Tines: Picking a Problem He Lived00:06:26 - Why Founders Beat Sales Teams00:11:18 - Spending 30–50% of His Week With Customers00:12:58 - The Refounding Moment Begins00:17:22 - The "Falling Off a Building" Analogy00:21:13 - Telling the Team and the Board00:24:38 - No Existing Customer Was Ever Forced to Migrate00:33:13 - Bootstrapping and the First Raise00:33:33 - Blossom Capital Shows Up at Their Office00:36:33 - How He Actually Picked Investors00:38:27 - Board as an Extension of the Team00:41:27 - Building a Fully Remote, Global Team00:43:18 - Biggest Challenge: "Nobody Cares"00:55:48 - The Wizard of Oz Moment00:58:38 - What Actually Drives Him00:59:48 - Advice to His Younger Self