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

Most founders know they need an Ideal Customer Profile. Fewer realize how much growth depends on getting it right.

In this special compilation episode of Not Another CEO, David brings together lessons from seven founders, CEOs, and investors who all reached the same conclusion: growth accelerates when you're crystal clear about who you serve.

The episode explores why broad ICPs slow companies down, leading to weaker messaging, scattered product roadmaps, and unfocused sales efforts. Guests share how they identified their ideal customers, the mistakes they made, and the tough decisions required to stay focused as they scaled.

Key Takeaways

• An ICP that only exists in your head isn't an ICP. Write it down and you'll often discover you're targeting multiple markets at once.
• Segment until it hurts. The best companies define their market so specifically that they can name every company that fits their profile.
• Your users are not always your customers. Understanding the difference can prevent years of wasted effort.
• Focus requires sacrifice. Sometimes the right decision is walking away from paying customers who don't fit your long-term vision.
• The best teams use data, not assumptions, to refine their ICP and identify their highest-value customers.
• Micro-segmentation is becoming increasingly important. The strongest go-to-market teams don't just define an ICP, they segment within it.
• Your ICP should influence every part of the company, from product decisions to marketing strategy to hiring plans.
  

Quote of the Episode

"If you try to sell to everyone, you really end up selling to no one effectively." - David Politis, Host of Not Another CEO Podcast

Guests Featured in This Episode:

• Marcus Ryu, Co-Founder & Former CEO, Guidewire — LinkedIn
• Tom Buiocchi, Former CEO, ServiceChannel — LinkedIn
• Craig Rosenberg, Chief Platform Officer, Scale Venture Partners — LinkedIn
• Zach Smith, Co-Founder & Former CEO, Packet — LinkedIn
• Melanie Fellay, Co-Founder & CEO, Spekit — LinkedIn
• Sean Henry, Co-Founder & CEO, Stord — LinkedIn
• Rohyt Belani, Co-Founder & Former CEO, PhishMe — LinkedIn
  

Chapters:

00:00 - Trailer
00:55 - Why your ICP is probably too broad
05:55 - The exercise that exposes a fake ICP
08:59 - "Segment until it hurts"
14:00 - Why your ICP is actually several smaller ones
17:22 - Your users aren't always your customers
20:08 - The real cost of firing the wrong customers
23:36 - Champions aren't customers
24:59 - Your ICP will change, and that's not failure

Most people assume starting a company is the hardest job in business.

Dan O'Connell has learned that taking over one can be even harder.

Dan's career has taken him from Google, where he joined when the company was 300 people, to founding TalkIQ before AI was cool, to helping scale Dialpad past $200M in revenue, and now to leading Front as CEO.

Not many people have been an executive at a big tech company, a founder, a high growth operator, and a hired CEO. Dan has done all four.

Front is a customer operations platform used by more than 9,000 companies to manage customer conversations across support, customer success, account management, and sales.

When Dan joined, the company had strong talent, a strong product, and strong customers. But growth had slowed. This episode is about what he did next and what he learned along the way.

Takeaways:

1. Focus reaccelerates growth:
   When Dan joined Front, his first move wasn't a product change or a new hire. It was getting brutally clear on who they serve, where they win, and explicitly what they were not going to do. That intentionality alone reaccelerated growth.
   
2. Speed is a competitive advantage:
   Dan introduced speed as a formal company value at Front and it remains polarizing two and a half years later. It doesn't mean reckless. It means faster decision-making, strong opinionated leaders, and fighting friction when it shows up. Any decision is better than no decision.
   
3. Taking over is harder than starting:
   You're inheriting history, culture, and legacy inertia and you can't take six months to build trust before making changes. You have to do both at the same time. As Dan puts it, you're flying the plane while rebuilding it.
   
4. Great leaders stay close to customers:
   In his first week as CEO, Dan got on customer calls, visited every office, and jumped in the support queue to answer tickets. The same thing he now requires of every executive he hires. The team is always judging you and nothing builds credibility faster than showing you're willing to do the work.
   
5. Platforms will outlast pure agents:
   After attending OpenAI's Frontiers Conference, Dan's contrarian take is that pure agent companies solving one workflow may get commoditized by OpenAI and Anthropic over time. His bet is on platforms and Front's position as the entry point for all customer conversations across channels, regardless of how the AI landscape evolves.
   

If you are a founder, operator, or CEO this episode is worth your time.

Quote of the Show:

"Taking over has been much harder than I thought. And it's usually from the behaviors and people side." — Dan O'Connell, CEO, Front

Links:
LinkedIn: https://www.linkedin.com/in/danoconnell/
Front: https://front.com

Chapters:
00:00 Trailer
01:15 Introduction
02:15 The One Thing That Had the Biggest Impact: Focus
05:00 Narrowing the ICP
07:30 The Operating Machinery That Keeps a Company Focused
13:00 Taking Over as a Non-Founder CEO
17:15 Flying the Plane While Rebuilding It
22:30 Platform vs. AI Agents
29:00 Building the Executive Team
42:00 The Biggest Challenge
47:30 Where Front Is in Three Years
49:00 Origin Story: From Southampton to Google to Founding TalkIQ
56:00 Two Career-Defining Moments & Advice to His Younger Self

Most founders talk about building a company but very few talk about what it actually costs.

Dan Teran knows both sides of that story.

In this episode, Dan shares how he built Managed by Q from the ground up, scaled a team that included nearly 1,000 frontline workers, gave equity to cleaners and handymen, navigated an acquisition by WeWork, and ultimately made the transition from founder to investor.

We talk about the systems behind great culture, why the best founders are usually obsessed with a problem long before they start a company, what most VCs get wrong when evaluating startups, and how AI is changing the economics of company building.

Dan is one of the most thoughtful operators and investors I've met, and this conversation is packed with practical lessons for founders at every stage.

Takeaways:

1. Great cultures are built through systems, not slogans: The strongest company cultures don't come from posters on the wall. They come from who gets hired, who gets promoted, what behaviors get recognized, and what standards leaders reinforce every day.

2. The best founders are deeply connected to the problem they're solving: Dan believes the most resilient founders aren't chasing trends; they're solving problems they've experienced firsthand. That personal connection helps them stay committed when things get difficult.

3. Success is usually the result of hundreds of small decisions: Managed by Q wasn't built through one breakthrough moment. It was years of learning, adapting, fixing mistakes, and making better decisions over time.

4. AI is changing how companies get built: Founders can now test ideas, build products, and reach customers faster than ever before. What once took teams of engineers and millions of dollars can often be done by a handful of people.

5. Building something meaningful still requires hard work: Technology may change, but the reality of company building hasn't. Every successful founder eventually faces uncertainty, setbacks, and difficult decisions. Persistence is still the only way through them.

Quote of the Show: ”If you're lucky enough to find a problem worth working on, that's where the fulfillment comes from.” - Dan Teran, Co-Founder & Managing Partner, Gutter Capital

Links:
LinkedIn: https://www.linkedin.com/in/danteran/
Website: https://www.gutter.cc/

Chapters:

00:00: Trailer

01:18: Meet Dan Teran: Founder, Operator, Investor

04:45: Building a Culture That Actually Scales

11:55: Why Every Employee Received Equity

18:15: The Story Behind the WeWork Acquisition

25:10: Life After Selling the Company

29:00: Starting Gutter Capital

39:00: How Dan Evaluates Founders

52:20: The Operating Blueprint for Startups

Why does your pipeline feel broken… when the real problem is your strategy?

In this episode, I sat down with my longtime mentor & friend Craig Rosenberg, Chief Platform Officer at Scale Venture Partners. Craig taught me how to build inside sales teams 20 years ago, and he’s still one of the sharpest minds in go-to-market strategy.

We break down why most companies are struggling to create pipeline, the power of ruthless micro-segmentation, why the old outbound “spam cannon” is dead, and what actually works right now including smart AI plays and unmistakably human experiences.

If you’re a founder or leader frustrated with pipeline, this is the conversation you need.

Takeaways:

• Your Pipeline Isn’t Broken Your Strategy Is: Most companies are going too broad instead of micro-segmenting their ICP on the other hand the winners are ruthlessly micro-segmenting their ICP around homogeneous use cases.
• Micro-Segmentation Is the New Superpower: Stop fearing you’ll miss pipeline by going narrow. Focus the entire GTM team on a tight subset of accounts with similar needs this unlocks consistent messaging, better win rates, and faster learning cycles.
• Talk to 10 People a Week in Your ICP: Whether you’re at seed or scaling, executives must get in the weeds. Have real conversations, pitch them, and ask for next steps. Gong calls and outsourced interviews aren’t enough. This is how you validate and refine your story fast.
• Use AI as a Multiplier, Not a Crutch: Leverage AI for custom market reports, personalised demos at scale, deep account research, and proprietary signals. But the real advantage comes from pairing AI with unmistakably human interactions in a market flooded with AI noise.
• High-Touch Human Experiences Are Back: Curated dinners, thoughtful direct mail, and once-in-a-lifetime events (like World Cup experiences) outperform digital spam. Buyers can feel when real care and intention went into the interaction.

Quote of the Show: ”Because now AI is about to flood the market, is what are those unmistakably human interactions you can have.” - Craig Rosenberg, Chief Platform Office, Scale Venture Partners

Links:

LinkedIn: https://www.linkedin.com/in/craigrosenberg/ Scale Venture Partners: https://www.scalevp.com/team/craig-rosenberg

Chapters:

00:00: Intro

02:45: Why Pipeline Feels Harder Than Ever

06:10: The Power of Ruthless ICP Micro-Segmentation

10:25: Special Forces Teams for New Market Expansion

14:40: What’s Changed in B2B Buying (2026 Reality)

19:15: Why the Old Outbound Playbook Is Dead

24:50: AI Tactics That Are Actually Working

29:40: The Unmistakably Human Differentiator

35:20: High-Impact Events & Experiences

42:15: Final Advice + How to Stay Ahead

Most founders think investors decide after the pitch but this investor says the decision is usually made in the first five minutes.

In this episode of Not Another CEO, I sat down with Jess Lin, Co-Founder & General Partner at Work-Bench, for a deep conversation on what actually separates great founders from everyone else.

Jess breaks down how investors build conviction in founders within minutes, why product-market fit has become harder than ever, and what most startups misunderstand about growth, fundraising, and becoming truly mission critical. The conversation also explores the emotional side of venture capital, imposter syndrome, building a venture firm, and the realities founders face between Seed and Series A.

From founder obsession and investor psychology to career risk and company building, this episode is a candid look into how elite investors think and what founders need to understand to build enduring companies.

1. Investors Often Decide Faster Than Founders Realise: Jess explains that initial conviction about a founder is usually formed within minutes. The rest of the process is often about validating or disproving that instinct.
2. Growth Alone Is No Longer Enough: Fast revenue growth has become table stakes. The real question investors ask now is: Would customers genuinely care if this product disappeared tomorrow?
3. Founder Obsession Matters: The best founders are deeply obsessed with the problem they’re solving. They see something others don’t and cannot stop thinking about it.
4. Venture Capital Is Emotionally Uncertain: Jess shares how difficult it is to know whether you’re actually “good” at investing because feedback loops in venture can take 10+ years.
5. Building a VC Firm Is Like Building a Startup: From branding and hiring to differentiation and operations, venture firms face many of the same challenges founders do when building companies.

It's better to be fast than to be right. Because if you're fast, if you just have more at bats, you will least be able to course correct. - Jessica Lin, Co-Founder & General Partner at Work-Bench.

Links:
LinkedIn: https://www.linkedin.com/in/jessicalin8
Work-Bench: https://www.work-bench.com/

00:00: Trailer

04:12: How investors evaluate founders in the first five minutes

09:35: The founder traits that create investor conviction

15:08: Why Series A has become much harder

20:44: What “mission critical” really means in startups

27:10: Product-market fit vs fast growth

33:26: Imposter syndrome in venture capital

39:41: Career advice, risk & serendipity

46:03: Why building a VC firm feels like building a startup

53:18: Final lessons for founders and investors