In October 2008, Michael Dermer had just closed a private equity round at a valuation that validated a decade of work. He had close to 900 employees and a solution wired deep into the Fortune 1000. Within a month, two of his three largest clients ceased to exist and the third needed a government bailout.

What followed was three years of twenty-hour days with no defined endpoint, no visible math, and no one to tell him when it would be over. A year earlier he had turned down an offer for the company at a number he still refuses to say out loud. Learning to stop thinking about that number was, in his words, the part of him that had to die.

Michael eventually got the company to the other side and sold it. Then a friend said one sentence in a coffee shop that redirected the rest of his life, and The Lonely Entrepreneur was born.

In this episode:

• What the first thirty days after a black swan event actually feel like from the CEO's chair

• The two rules he gave his team when the plan stopped working

• Why he insists he never felt lonely, even while building a company named for loneliness

• The letter his business partner wrote about him, read aloud for the first time

• How he now tells founders to find markets that are worth zero today

• Why he believes AI is a 2008-scale reset and what skills survive it

• What he would say to himself on the worst night in the valley

Subscribe to Through the Valley wherever you listen. New episodes on YouTube, Spotify, and Apple Podcasts.

Find Michael at lonelyentrepreneur.com.

EPISODE CHAPTERS

00:00 The valley

02:50 October 15, 2008

04:30 Two of his three biggest clients disappear

07:58 The offer he turned down

10:12 Three years, 20-hour days, a 1-in-10 shot

15:04 The letter

17:29 "Who here is a lonely entrepreneur?"

20:11 Why he says he never felt lonely

39:00 Why AI feels like 2008 again

50:57 The worst night in the valley

At 28, Jordan Fliegel had a career-ending injury behind him, thirty employees in front of him, and a startup he loved so much he lived across the street from the office so he could be the first one in. Then his board told him they were replacing him as CEO, and offered him three to five million dollars at a higher valuation if he'd stay quietly and help pick his own replacement.

He said yes. Not because he agreed with it, but because saying no meant firing the people he called family. He's never talked about it publicly until now.

Jordan is the founder of CoachUp, former co-CEO of DRAFT, and now the founder and CEO of Acquisition Lab, where he helps people buy small businesses instead of starting them. In this conversation with Mark Phillips he walks through the whole valley: the demotion, the year he spent as a president whose title meant nothing, the nine months he slept in a Manhattan office while his next company was insolvent, and the day he finally came back and removed the investors who removed him.

In this episode:

• The napkin math that shows exactly when your investors' incentives stop matching yours
• Why he ran through Boston in tears to a mentor's office with no appointment
• What it feels like to sit in meetings where every good idea you offer undermines your own successor
• How he told ten employees the money was gone, and what he had to say to the one he couldn't save
• The letter his mentor wrote him, read out loud for the first time
• Why he took a company from "we can't pay our bills" to a $48M exit
• The Jocko Willink rule he now applies to every piece of bad news

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Watch on YouTube, listen on Spotify and Apple Podcasts.

Timestamps:

00:00 Intro

02:21 CoachUp was his identity

03:48 What the stress was doing to his body

06:59 When investor incentives stop matching yours

07:53 The middle range, where founders get replaced

08:47 The board’s offer, and helping pick his successor

09:42 Why he said yes: the thirty people he hired

12:24 The napkin math on preferred stock

15:55 President and chairman, “which means nothing”

17:04 Every good idea undermining his own replacement

19:04 What boxing taught him about getting hit

20:02 Running through Boston to his mentor’s office

21:40 The letter, read out loud

25:24 Telling ten employees the money was gone

26:00 Out of money, and the flight to California

26:56 Buying back in, and the turnaround

33:20 Start it, join it, or buy it

35:17 Fall in love with the problem

41:27 Building Acquisition Lab

46:08 The injury that ended his playing career

In the fall of 2022 Brandon Aversano was 30 years old, away on a trip in California, and found it himself in the middle of the night. Thirty minutes after an ultrasound the chief of urology walked into the room and told him there was a 99% chance it was testicular cancer. His first thought wasn’t about himself. It was how he was going to tell his mom.

Nothing could be known before surgery. Three weeks of sitting with whether it was in one spot or everywhere. His dad had prostate cancer the year before. Brandon had built an identity on competence, distinguished scholar, Deloitte, JetBlue, JP Morgan, and the one thing he suddenly couldn’t do was be the capable one. He went on disability the day after scheduling surgery and had free time for the first time in a decade.

Mark Phillips sits with Brandon on what that season cost and what it built: the medical debt that horrified a father who hated debt, the trip to Jewelers Row with his grandmother’s jewelry where strangers offered twenty cents on the dollar, the 401k he emptied into a company, the $40,000 mobile app his co-founder told him to scrap, and the surgeon who said the book on whether it comes back is already written and he doesn’t get to read the last chapter for five years.

In this episode:

- The 24 hours between finding it himself and hearing the number

- Why telling his parents was harder than hearing the diagnosis

- What three weeks of not knowing does to someone who built his life on competence

- Jewelers Row, twenty cents on the dollar, and the moment Alloy became obvious

- The customer who asked to speak to the founder and had them both crying on the phone

- Learning to control the controllable, and the chapter he doesn’t get to read for five years

- The letter from a friend of eighteen years, and what he’d tell himself on the worst night

Subscribe to Through the Valley on YouTube, Spotify, and Apple Podcasts. Brandon’s company, The Alloy Market, sends a free evaluation kit to anyone looking to sell gold.

Timestamps:

00:00 Intro

02:33 The night he found it himself

04:09 Why telling his mom was the hardest part

05:48 Three weeks of not knowing

06:54 An identity built on competence

07:48 Is that really your purpose?

09:38 Jewelers Row and twenty cents on the dollar

12:02 The lightning bolt that became Alloy

15:48 The golden handcuffs

17:05 The space the diagnosis created

19:01 Scans, and the chapter he can’t read for five years

20:36 What control means to him now

27:25 The $40,000 app his co-founder told him to scrap

29:16 What happened to the achiever

31:10 The customer call that had them both crying

33:28 Why he wouldn’t trade cancer for anything

34:29 The letter from a friend of eighteen years

39:08 What he’d tell himself on the worst night

42:37 Mark on losing his mom

45:39 The GoFundMe he started after his diagnosis

Justin Gurland arrived at rehab at eleven at night, three thousand miles from everyone he knew. He woke up the next morning in Los Angeles on Super Bowl Sunday, 2008, gave himself the finger in the mirror, and watched the Giants beat the undefeated Patriots. Then the staff turned off the game, walked everyone into a group room, and asked what each of them believed in.

He was twenty-five. He had no community, no sober person anywhere in his life to point at, and no idea what the question meant. What he said was that the Giants had just won and he could hold on to that for now. He describes the moment as meaningless on its face, a football game, a team he wasn't on. It was also the only thing he had.

Mark Phillips sits with Justin eighteen years later, five blocks from The Maze, the members club he opened in the Flatiron where hundreds of New Yorkers pay to belong to a building with no alcohol in it. They talk about the sister who told him she couldn't take it anymore, the letter his father hand-wrote for this episode, the Grateful Dead lyric he keeps returning to, and the question he still can't answer: why the shame attaches to getting sober instead of to the damage.

In this episode:

• Why he says his sister saved his life, and what happens to people who never get that conversation

• The Godfather scene he read a month before everything came apart, and why it stayed with him

• What he actually said when a counselor asked the room about God

• Playing a kids' board game in treatment and feeling his side hurt from laughing for the first time in years

• What his father wrote about Justin's lowest moment, and where his relationship with him sits now

• Why there is shame in getting sober and none in the harm that came before it

• The alcohol-free movement he did not know existed until it was growing in front of him

• What he would say if he could sit with himself on the worst night: take this in, and get to work

Subscribe to Through the Valley on YouTube, Spotify, and Apple Podcasts. You can find The Maze at themazenyc.com, on Instagram at @themazenyc, and on LinkedIn.

Timestamps:

00:00 Intro

02:32 January 2008, and what the end looked like

03:56 The sister who would not let it go

04:24 Never having known a sober person

05:13 The book he was reading when it turned

08:10 What happens without someone in your corner

09:07 Through the valley: how dark it got

09:48 Arriving at rehab on Super Bowl Sunday

11:10 Borrowing hope from a football team

12:23 Something insignificant that carried enormous weight

13:10 Faith as an evolving process, and what seeking means

15:16 Laughing until his side hurt for the first time in years

17:47 The moment with his brother

18:45 What his father wrote about that season

20:48 What the word shame actually means here

22:57 Shown the light in the strangest of places

25:06 Really being awake

36:13 How The Maze started with coffee

38:20 Still reeling from Covid, and what fake connection looks like

43:01 What he would say to himself on the worst night

45:13 Who The Maze is actually for

For 20 years, Charlie O'Donnell was the most findable investor in New York. Email on the front page of his site, pitch me anything, come to the dinner. Then in May 2023 he wrote a sentence announcing his last venture deal and stopped.

The market didn't push him out. Most people in venture keep raising because it's a good job and there's always a next fund. Charlie ran Brooklyn Bridge Ventures as a solo first-check investor across more than 100 companies, and when he looked at the two available ways to keep doing it into his 40s (hire a younger version of himself, or stop looking at anything pre-revenue) he decided he'd rather not do the job at all than do it that way.

Mark Phillips sits with Charlie on what it costs to hold a career loosely: the ice cream shop that went to zero and the conversation he never had with those founders, the marathon he ran badly and blamed on the wind, the 80 days in the NICU where three term sheets got signed, and the firefighter father who played tennis in the morning and did tax returns in the afternoon and was content.

In this episode:

• Why Charlie stopped raising funds while the option to continue was still open

• The tradeoff he now tells every founder about before they take a check

• How to hold "good investor" as a job rather than an identity

• What 16 collapsed triathletes reveal about experienced high performers

• The rounded-up revenue number that quietly ends a fundraise

• What his father's illness taught him about asking what a person actually needs

• The one thing he realized far too late about being a partner at home

Subscribe to Through the Valley on YouTube, Spotify, and Apple Podcasts. Charlie's book, Founder Unfriendly: What Investors Won't Tell You About Getting Funded, is available wherever you buy books, and his newsletter has been running at thisisgoingtobebig.com since 2004.

Jason Jaggard is the founder of Novus Global, one of the biggest executive coaching firms in the world whose coaches work with Global Executives, professional athletes, and Grammy-winning artists. But at 30, his life collapsed. In a single year, he quit a great job, lost 90% of his revenue, and watched his most important relationship fall apart. We talk about what broke, why it broke, and how that year became the foundation for the firm he leads today.

In this first episode of Through the Valley, Jason talks with Mark Phillips about the night he collapsed on his apartment floor, the "cold war" he entered with God, and how the tools he found in his darkest season became the foundation of a coaching firm that now serves some of the most influential leaders on Earth.

They cover why blame keeps you stuck, why self-pity is a drug, the difference between psychological safety and psychological strength, and why community is the closest thing to a bulletproof vest a founder can wear.

Through the Valley is hosted by Mark Phillips, founder of 11 Tribes Ventures, and explores the seasons of loss, failure, and doubt behind remarkable careers.

CHAPTERS
0:00 - Cold open: "I was hurting myself, and I was using them to do it"
2:11 - The question Jason's whole life has circled: what am I capable of?
3:46 - Quitting the job, losing 90% of revenue, the relationship imploding
5:11 - The collapse: "I wept and wailed"
6:46 - The small voice that says it's going to be okay
8:17 - Prayer as defibrillator
9:37 - A cold war with God
11:18 - Control, and why control and love can't coexist
12:54 - The 12-step program that changed everything
15:26 - The valley makes you who you are
16:53 - Blame, and discovering radical responsibility
19:06 - "Who needs heroin when you can feel sorry for yourself?"
20:00 - Shampoo-commercial coaching and the barbed wire blanket
20:34 - The leaders who don't realize they're in the valley
21:31 - "This isn't fun anymore"
22:03 - Every new level of the video game demands more
23:44 - How much margin should a leader have?
26:47 - Passion means suffering. Choose yours
27:34 - Be the buffalo: run into the storm
29:42 - Psychological safety vs. psychological strength
31:43 - A letter from Mateo
32:45 - Loneliness is the most dangerous warning light
33:45 - The bat signal: 18 cars in two minutes
36:15 - Mark on losing his mother
37:02 - How to actually build community
38:42 - What Jason would say to his younger self on his worst night
40:38 - Closing prayer