Not Another CEO Podcast

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 Media

Guest Featured in This Episode: Alex Konrad, Founder, Upstarts Media
LinkedIn: 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 - Intro
02:01 - How Alex decides who to cover
11:37 - Why Alex left Forbes to build Upstarts
17:52 - The number one trait of successful founders
19:56 - Founder cycles and finding your one superpower
27:05 - The Midas List and what makes a great investor
34:35 - Storytelling and the trillion-dollar outcome
40:23 - Building Upstarts solo and bootstrapped
42:14 - The loneliness of being a solo founder
44:26 - Crazy customer stories and "Elon-level" security
49:16 - Terminally online founders
54:59 - 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, Tines

Guest Featured in This Episode: Eoin Hinchy, Co-Founder & CEO, Tines
LinkedIn: 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 - Introduction
00:02:35 - Best Decision at Tines: Picking a Problem He Lived
00:06:26 - Why Founders Beat Sales Teams
00:11:18 - Spending 30–50% of His Week With Customers
00:12:58 - The Refounding Moment Begins
00:17:22 - The "Falling Off a Building" Analogy
00:21:13 - Telling the Team and the Board
00:24:38 - No Existing Customer Was Ever Forced to Migrate
00:33:13 - Bootstrapping and the First Raise
00:33:33 - Blossom Capital Shows Up at Their Office
00:36:33 - How He Actually Picked Investors
00:38:27 - Board as an Extension of the Team
00:41:27 - Building a Fully Remote, Global Team
00:43:18 - Biggest Challenge: "Nobody Cares"
00:55:48 - The Wizard of Oz Moment
00:58:38 - What Actually Drives Him
00:59:48 - Advice to His Younger Self

Most people think experience is your greatest advantage. Ronnen Harary believes it can become your biggest blind spot.

In this episode, Ronnen Harary, Co-Founder of Spin Master, shares the lessons behind building one of the world's most successful toy and entertainment companies, the creator of global brands like Paw Patrol, Bakugan, Air Hogs, Rubik's Cube, and Etch A Sketch.

From turning down a $100 million Hollywood deal he now regrets, to explaining why it's riskier not to bet on yourself, Ronnen unpacks the mindset that helped Spin Master grow from three friends with an idea into a multi-billion-dollar public company.

Key Takeaways:
1. The Power of Not Knowing: Sometimes experience becomes a limitation. Ronnen explains why the lack of conventional wisdom helped Spin Master create products that industry veterans had already dismissed, and why trusting your instincts matters more than following what everyone else believes.

2. Bet on Yourself Early: Your 20s are a unique window to take meaningful risks. As responsibilities grow, so does the cost of leaving a stable career. Ronnen argues that waiting until you feel "ready" often means you never start at all.

3. Create Your Own Luck: Luck isn't something that happens to you. It's something you earn by staying in motion, building relationships, and consistently putting yourself in situations where unexpected opportunities can find you.

4. Trust Your Instincts: The same experience that helps you build a successful company can eventually cause you to overthink. Ronnen shares why he believes your intuition is often a better guide than your intellect when making the biggest decisions.

5. Build a Culture of Ideas: Some of Spin Master's best ideas came from meetings that everyone else wanted to cancel. Ronnen explains why protecting time for open discussion and pulling the right people into the room fuels creativity and better decision-making.

Quote of the Show:
"The power isn't in not knowing. It's in not letting your intellect override what you know internally." – Ronnen Harary, Co-Founder, Spin Master

Guest Featured in This Episode: Ronnen Harary, Co-Founder, Spin Master
LinkedIn: https://www.linkedin.com/in/ronnen-harary-99b13370/
Spin Master: https://www.spinmaster.com/en-US/
No Experience Necessary: https://www.penguinrandomhouse.com/books/789812/no-experience-necessary-by-ronnen-harary/

Chapters:
00:00:00 — Trailer & Introduction
00:02:05 — The 32-Year Tri-Founder Partnership
00:05:34 — "The Power of Not Knowing" & The Air Hogs Story
00:09:00 — The $100M Bakugan Regret
00:10:26 — Betting on Yourself in Your 20s & Inverse Risk
00:16:44 — Early Parent Support
00:18:47 — Becoming a "Grinder"
00:22:46 — Operational Discipline
00:27:14 — Making Your Own Luck: The Flick Tricks Story
00:33:40 — "Tethered Freedom" & Owning Your Culture
00:35:20 — Seeking Micro-Mentors & Writing "No Experience Required"
00:38:46 — The Decision to Take Spin Master Public
00:41:28 — The Origin Story of Paw Patrol
00:47:08 — Evolution of the Toy Industry
00:49:45 — Future Outlook for Spin Master
00:50:37 — Ronen’s Background
00:53:39 — Early Hustles
00:58:03 — Core Drive
00:59:13 — Workaholism, Burnout, and Health Sacrifices
01:04:03 — Advice to Younger Self

Most companies that start the FedRAMP process never finish it.

Irina Denisenko built a business on getting you through it in 90 days, and said so, loudly, when everyone told her not to.

Irina is the founder and CEO of Knox Systems, a company that gets software companies FedRAMP certified — the federal government's exhaustive cybersecurity authorization required to sell to agencies like the Pentagon — in 90 days instead of the usual multi-year process.

Two years in, Knox has raised over $30 million, crossed 100 customers, and counts Adobe among them. Before this, Irina was COO of Class Technologies, where she had to get her own company FedRAMP certified and ended up acquiring an already, authorized company just to get through the process. She later spun that capability out as Knox.

Here were my biggest takeaways:
1. Trust that you know your market better than the room does: When advisors pushed Irina to soften her tagline, she refused. "I know my market. I've lived this problem," she told me.

2. Turn a cost center into a revenue unlock: Irina assumed her first customers would come through CISOs. Instead, her first ten came from calling friends who ran companies. The real unlock was reframing FedRAMP: it's not a compliance expense, it's access to a market a company was previously shut out of entirely.

3. Make your investors work for you, even when you're not raising: Irina stays close to her investor network specifically because boardrooms are where FedRAMP tends to get dismissed as too slow to bother with. She's built a habit of asking investors to correct that in the room on her behalf.

4. Kill a bad bet before you defend it: Knox made an early bet on a specific AI approach to auto-remediate security vulnerabilities. The technology wasn't ready yet, and by the time that was undeniable, they'd already sunk real time and money into it.

5. Never underpay your best people: Irina calls her hiring approach "Delta Force" — senior only, nobody walking in without years of reps elsewhere. Her rule on comp: she's never once regretted overpaying for the right person, and calls the opposite mindset "pennywise, pound foolish."

Quote of the Show:
"If you know your market, you should know how to talk to them. And if you don't know your market, you go figure out your market first.” - Irina Denisenko, Founder & CEO, Knox Systems

Guest Featured in this Episode:
Irina Denisenko: https://www.linkedin.com/in/irinadenisenko/
Knox Systems: https://knoxsystems.com/

If you enjoy the episode, please like and subscribe on your favourite platforms and share with your network.

We also break this episode down into a full write-up on Substack, with the exact playbook Irina used to build a go-to-market motion around a tagline everyone told her to drop, we're building out a full library of playbooks and lessons from every episode on Substack.

Chapters:
00:00:00 — Intro: Irina Denisenko & Knox Systems
00:02:13 — The "FedRAMP in 90 Days" Tagline
00:06:34 — Building In-Person Across 3 Cities
00:08:52 — Hiring Only "Delta Force" Talent
00:11:41 — Revenue Per Employee in the Age of AI
00:17:10 — How She Vets a Delta Force Hire
00:25:57 — Never Regretting Overpaying for Talent
00:31:26 — Landing the First 10 Customers
00:42:41 — Investors as Her Best Referral Channel
00:47:43 — "Who Cares About This Market"
00:52:31 — The Valuation Hangover
01:02:16 — Scrapping a Year of AI Work
01:05:29 — From the Soviet Union to Founder
01:16:41 — Closing Advice: Integrity Above All

I've interviewed over 100 founders and CEOs on Not Another CEO. I've asked them about their hardest days, their biggest regrets, and the sacrifices they made to build what they built. I never thought I'd be the one in that seat.

This week, my own kids flipped the mic on me. Sammy and Noah wrote their own questions and interviewed me for the show, and I had no idea what was coming. We covered the worst week of my career, firing people I actually liked, the sacrifices I made that I'd still make again, and the moment my son stumped two successful CEOs on a live stage with a single question.

Here's what we got into:

Where it started: My father, their grandfather, built companies my whole life, and he put me on the BCC of every email he ever sent so I could learn the business before I had a job in it. My actual first paycheck came from a summer carrying furniture up four story walk ups for a moving company in New York.

The worst week of my career: one week in 2019 where we lost our biggest customer, our incoming CRO backed out the day before he was supposed to start, I found out I wasn't winning an award I really wanted, I tore my Achilles, and I missed a family trip to Israel, all in the span of five days.

Firing people I liked: I've fired hundreds of people over 20 years, including good friends. My kids asked how I could do that, and we talked about why it's actually the kinder move when it's done right.

The sacrifice question: I missed my son's first steps building BetterCloud, and I left the hospital right after my younger son was born to go straight to a VC meeting. My kids wanted to know if I'd still make that call today.

Comparing myself to other CEOs: yes, I still get jealous scrolling LinkedIn. It was worse when I was actually running BetterCloud and too deep in the weeds to see anything but my own world.

How I define success: the same answer my son got out of me at our first ever live show, the one that stumped Kass and Mike Lazarow in front of a packed room.

This is a different kind of episode for the show, and it might be one of my favorites. Thanks for listening, and thanks to Sammy and Noah for the toughest interview I've ever done.

Quote of the Show:
"The way that I define success is being able to meaningfully impact other people's lives while significantly benefiting your own life." — David Politis, Host, Not Another CEO Podcast

Chapters:
00:00:00 - Trailer
00:02:22 - BetterCloud's Biggest Lesson
00:04:52 - What Inspired Me to Want to Be a CEO
00:07:12 - My First Job
00:10:14 - Pitching BetterCloud to My Own Kids
00:15:21 - What 100+ Interviews Taught Me About Building a Company 00:20:31 - AI and the Skills That Won't Get Replaced
00:23:37 - The Hardest Days
00:29:35 - Still Bad At It, Jealous of Other CEOs
00:33:13 - How I Define Success
00:41:29 - The Sacrifice Question
00:46:47 - Trust Your Gut

Most founders assume the loneliness fades once the company succeeds.
It doesn't. If anything, it gets quieter and harder to name.

In this special compilation episode of Not Another CEO, David brings together lessons from nine founders, CEOs, and investors who have built, scaled, sold, and advised some of the most recognizable companies in tech.

The conversation moves through why the seat is lonely in the first place, the false belief that you are the only one carrying it, and what the best CEOs actually build around themselves once they stop trying to carry it alone.

Key Takeaways:

• Loneliness at the top isn't a personal failing, it's baked into the structure of the job: unpopular decisions, imperfect information, and a team that only ever sees half the picture.
• The belief that you are uniquely alone in your struggles is common and almost always wrong.
• Even the most people-first, culture-driven CEOs cannot fully escape the isolation of being the one who stays in the seat while everyone else eventually moves on.
• Founder loneliness is a default, not a fixed destiny. A co-founder, a coach, or a peer group can change the default entirely.
• The most effective support comes from someone with independent context on your business and your team.
• Support systems show up in real outcomes, not just in how someone feels.
• The founders who say they never felt the loneliness usually point to the same thing: a spouse, a family member, or a peer they could call and be fully honest with.

Quote of the Episode
"Your team has no conception of how lonely it is to be the CEO."
— Adam Dell, Founder & CEO, Domain Money

Guests Featured in This Episode:

• Marcus Ryu, Co-Founder & Former CEO, Guidewire — LinkedIn
• Adam Dell, Founder & CEO, Domain Money — LinkedIn
• Chieh Huang, Co-Founder & Former CEO, Boxed — LinkedIn
• Nick Mehta, Co-Founder & Former CEO, Gainsight — LinkedIn
• Nadia Boujarwah, Co-Founder & Former CEO, Dia&Co — LinkedIn
• Chip Hazard, General Partner & Co-Founder, Flybridge — LinkedIn
• Kathryn Minshew, Co-Founder & Former CEO, The Muse — LinkedIn
• Mike Grossman, CEO (6x) & Author, Failure Is an Option — LinkedIn
• Kyle Porter, Founder & Board Chair, Salesloft — LinkedIn
  
  Chapters:
  00:00 – Trailer

  00:48 – Intro

  02:20 – Marcus Ryu

  03:34 – Adam Dell
  04:57 – Chieh Huang

  05:59 – Nick Mehta

  07:26 – Nadia Boujarwah
  08:43 – Chip Hazard

  10:10 – Kathryn Minshew

  12:34 – Mike Grossman

  15:38 – Kyle Porter

  16:38 – Closing Thoughts

Everything you think you know about why startups succeed might be wrong

In this episode, Mike Grossman, six-time CEO and mentor to first-time founders across Silicon Valley, breaks down what thirty years of running companies actually taught him.

From the $200 million counteroffer that blew up his first company, to why he believes luck accounts for 80 to 90 percent of every outcome, Mike pulls back the curtain on what nobody tells you before you take the job.

If you think success is mostly about hard work and good decisions, this conversation will make you rethink how you handle risk, pivots, and your own sense of control.

Key Takeaways:

Build a System to Find the Truth: Your direct reports won't always tell you what's really happening, whether they're afraid to or simply don't know themselves. Cut through the management chain and find the people who will tell you the truth.

Hold Your Plans Loosely: A plan is obsolete the moment you make it. The goal isn't a perfect plan, it's a planning mindset flexible enough to adjust without losing the team.

Stop Whiplashing Your Team: What feels like velocity to a founder can feel like chaos to everyone else. Pivot too often and even your own board will stop trusting your judgment.

Beware Your Own Kool-Aid: Believing your company is destined for outsized value can cost you the deal in front of you. Mike turned down a $40 million offer and countered at $200 million. He got neither.

Luck Runs the Table: Mike believes 80 to 90 percent of a company's outcome comes down to luck, not execution. Focus on what you can control and let go of the rest.

Watch Out for the Debilitating Win: Founders who succeed once often can't understand why the second company isn't working the same way. It usually wasn't the formula. It was luck.

Nobody Talks About the Loneliness: Nearly every first-time CEO Mike coaches struggles with anxiety and isolation, and most feel they can't show it to their own investors.

Quote of the Show: Plans are useless because whatever plan you make is immediately out of date and you have to make adjustments to it. But if you don't make any plan and you just do it on a seat of the pants basis, everything is kind of ad hoc, you end up jerking the company around and people get frustrated.- Mike Grossman, Entrepreneur and Author

Connect with Mike:
LinkedIn: https://www.linkedin.com/in/migrossman/
Book Failure is an Option: https://share.google/9DUEHB6596Eb1uXAa

Chapters:
00:00 — Intro

02:21 — The One Thing Mike Would Do Again At Every Company

08:39 — Bill Campbell's Rule

20:13 — Plans Are Useless, Planning Is Indispensable

25:19 — The Pivot His Board Rejected

26:58 — All Of Them Struggle With Their Mental Health

30:47 — The $200 Million Deal He Blew Up

38:58 — Luck Accounts For 80 To 90 Percent

44:17 — The Debilitating Win

54:16 — Remembering The Coach Of Silicon Valley

"You cannot outsource acquiring those first ten customers. You can't do it."

In this episode of Not Another CEO, David breaks down the six tactical ways he's used, three separate times now, to land his first customers from zero. From holding a pizza party for international students to handing out fliers at the Atlanta airport taxi stand to asking his own uncle to buy a phone system, David gets specific about what actually works when you're starting from nothing.

What's covered:

-Why getting your first customers is harder now than ever, even though building product has never been easier
-Reconnecting with former employers and coworkers who already trust you
-How to actually use your investor network, even at the angel stage
-Why showing up in person at trade shows and meetups still beats almost everything else
-Building in public on social media, even when almost nobody engages at first
-The one BCC email that got David a customer and an important hire at the same time
-How to do cold outreach that people actually respond to
-Why none of these six tactics scale, and why that's exactly the point

If you're a founder still chasing your first ten customers, this one's for you.

We cover more topics like this in full playbooks on our Substack. Subscribe to get the tactical deep dives, not just the highlights: notanotherceo.substack.com

Chapters:
00:00 - Trailer
00:44 - Why Finding Your First Customers Is Harder Than Ever
05:20 - Tactic 1: Reconnect with Former Employers & Coworkers
06:28 - Tactic 2: Tap Into Your Investor Network
08:14 - Tactic 3: Show Up in Person (Trade Shows & Meetups)
09:42 - Tactic 4: Build in Public on Social Media
11:02 - Tactic 5: Tell Your Friends and Family
12:02 - Tactic 6: Cold Outreach Done Right
13:53 - Why Doing Things That Don't Scale Is the Entire Point

Everything you think you know about venture capital might be wrong.

In this episode, Jeff Becker, General Partner at Antler New York, breaks down the brutal, hidden realities of the startup world.

From why investors care more about your childhood psychology than your pitch deck, to why a $500 million exit can actually be a massive disappointment to a fund, Jeff pulls back the curtain on how venture capitalists actually math out risk.

If you are operating with a broken mental model of how fundraising works, this conversation will completely reshape how you build, pitch, and scale your business.

Key Takeaways:
Pitch Yourself, Not the Product: Early-stage investors bet on the person first. Master your personal story of resilience before you even open your slide deck.

Understand Fund Math: A $500 million exit does not return a large fund. You must build toward a multi-billion-dollar scale to make your investor's job a success.

Expect the Volume Game: Firms like Antler build "engineered serendipity" by backing 200 early-stage founders at once, relying on massive diversification to find a breakout winner.

Take Money Off the Table: Luck and market shifts rule the startup graveyard. When liquidity windows open, secure your personal financial safety.

Storytellers Win the Cash: Being a great operator is not enough. You must be able to compress the gap between reality and future potential to get funded.

Give Investors Specific Homework: Investors want to work for you, but vague asks get vague results. Give them transparent, direct tasks so they can help you win.

Quote of the Show:
"If I'm not working as hard as the founders, none of them are going to want me on their cap table." - Jeff Becker, General Partner, Antler

Guest Featured in This Episode:
Jeff Becker, General Partner, Antler (New York)
LinkedIn: https://www.linkedin.com/in/jeffreylbecker/
Antler: https://www.antler.co/

We also break this episode down into a full write-up on Substack, with the exact playbook Scott used to fix the culture and rebuild the strategy from scratch, we're building out a full library of playbooks and lessons from every episode on Substack.

Chapters
00:00 — Intro
02:00 — The Maniac Framework
09:00 — Why Childhood Matters
15:00 — Jeff's Origin Story
20:00 — Angel Investing Days
26:00 — The Role of Luck
33:00 — AI & One-Person Companies
41:00 — Fund Math & Dilution
46:00 — Storytellers vs. Operators
51:00 — "I Work For You"

Majority founders only start thinking seriously about their next round when they’re already running low on cash. By then, you’re not really raising; you’re begging.

On this week’s episode of Not Another CEO, we sit down with Nick Moran, Co-Founder and General Partner at New Stack Ventures. Founded in 2015, New Stack manages close to $100 million and leads pre-seed and seed rounds with a unique mission: backing "The Outsiders," who are ambitious founders building category-defining companies outside the Bay Area and outside the obvious networks. Nick also hosts Full Ratchet, one of the first venture capital podcasts ever made, now closing in on 1,000 episodes. I know how hard it is to stay consistent with a podcast. Doing it for over a decade is a different level.

Nick shares his brutal honesty on what it actually takes to build a venture-backed business, why he tells founders to build their next pitch deck the day they close their current round, and how he evaluates the intangibles that traditional VCs completely miss.

• The Next Round Plan (NRP): Why fundraising is a continuous narrative, not a sporadic event. Nick breaks down how to align on business models, track leading indicators over lagging revenue, and build a highly targeted investor list early.
• Desire Beats Talent: Most VCs look for the "Peyton Mannings" of tech, meaning those who are obvious, expensive, and pedigreed. Nick hunts for the "Tom Bradys," founders with a chip on their shoulder, undeniable ambition, and the drive to beat long odds.
• Bad News Travels Fast: The ultimate trust-builder between a founder and a VC. Going dark creates anxiety; transparency during a brutal quarter is exactly what inspires an investor to throw you a lifeline.
• The Power of Being an "Outsider": Building in cities like Charlotte, Nashville, Dallas, or Chicago isn't a disadvantage. When the herd concentrates in the Bay Area, the best, most capital-efficient opportunities are often found where others aren't looking.
• Where the Smart Money is in AI: The shift from infrastructure to proprietary data. Nick explains why the next massive wave of AI value belongs to domain experts who control the data locked behind enterprise firewalls.

Quote of the Show:

“Do you want to be great or do you want to be happy?… You better be ready for the big game here because this is not an easy path. We're not going to be happy for the next ten years.” — Nick Moran

Connect with Nick:

• LinkedIn: https://www.linkedin.com/in/nick-moran-a738503/
• New Stack Ventures: https://www.newstack.com/
• The Full Ratchet: https://www.youtube.com/@nicholasmoran3095/featured

Chapters :
00:00 Trailer

01:30 Welcome Nick Moran, New Stack Ventures

03:54 Why desire is the ultimate founder trait

10:02 First impressions and the dating phase of investing

15:34 Founder-VC fit is like marriage

20:56 The Outsiders thesis and building a national network

27:48 Inside the Next Round Plan (NRP)

32:20 Communication, bad news should travel fast

39:00 What founders misunderstand about the VC side of the table

42:10 Where the smart money is moving in AI & Closing thoughts