The Second Mountain: What Comes After You’ve “Made It”
Michael Sonnenfeldt has spent decades working with entrepreneurs who sold their companies. He founded Tiger 21, a peer network for high-net-worth individuals, and has observed hundreds of founders navigate the aftermath of a liquidity event. His observation cuts against everything we assume about success: “The day after you sell, you might have a lot of money but you’ve lost the platform that allowed you to feel successful.”
This is the dirty secret of the first mountain. And it explains why the second one matters more.
What Is the Second Mountain?
The concept comes from Scott Galloway, who picked it up from David Brooks’ book of the same name. Galloway describes it simply: “It’s basically what happens after you achieve success. A lot of people are totally fucking lost. Because when you achieve the thing you want, you assume you’re going to feel fulfilled and you feel empty.”
The first mountain is the one we’re all taught to climb. Get the degree. Build the company. Make the money. Earn the recognition. It’s the mountain of resume virtues, external validation, and measurable accomplishment.
The second mountain is different. It’s the climb toward meaning, service, and contribution. Sam Parr illustrated it with Joe Gebbia, the Airbnb co-founder. “He’s the 96th richest man in America. He started Samara, an ADU company. He wanted to prove it wasn’t luck. But then he joined the government to fix the retirement process for workers. Now he’s the Chief Design Officer of the USA. That’s an inspired second mountain. It has impact and scale.”
The shift isn’t about retiring. It’s about redefining what you’re climbing toward.
The First Mountain Trap: Why 20% More Is Never Enough
There’s a peculiar statistic that reveals something uncomfortable about human nature. Michael Sonnenfeldt has observed it across every income level: “Whether you ask people who earn seventy thousand, seven hundred thousand, or seven million dollars a year how much more do you have to earn to be happy, the number is something like 20% more no matter where you are.”
The goalposts move on a predetermined schedule. We always need a little more.
Tim Ferriss has watched this pattern destroy his friends’ plans. “A lot of my friends were like, ‘Once I have five million, I’m going to create a woodworking shop in Oregon and just do the things I really enjoy doing.’ And then they get to five, and then it goes to 10, then it goes to 50, then it goes to 100, then it goes—it just keeps going.”
Why does this happen? Ferriss points to identity: “The only thing they know how to do well, where they feel confident, and furthermore they have their self-worth wrapped up in, is putting points on the scoreboard in the form of money.”
When your entire sense of capability is tied to a single game, you never stop playing. Not because you love the game, but because you don’t know any others.
Post-Exit Depression: The Shock Nobody Talks About
Selling a business is supposed to be the happy ending. The financial stories we tell ourselves assume that liquidity equals liberation. But Sonnenfeldt has witnessed something more complicated.
“The day after you sell it you have a lot of money but you might be alone. You might have an assistant but you don’t have a thousand employees. You don’t have anybody laughing at your jokes anymore. You might even have to get your own coffee. And everybody around you thinks that you’re wealthy and successful but you’ve lost the platform that allowed you to feel successful.”
There’s also what Tiger 21 calls “sticker shock.” The math is brutal. Sonnenfeldt walks through it: “If you take a business that was making 3 million dollars and you sold it for 20 million dollars and you paid the taxes, now you have 16 million. But if you buy bonds at 2 percent, you’re now making 320,000 on that same capital that was generating 3 million dollars before. You’ve lost 90 percent of your earning power.”
Jack Smith sold Vungle for $800 million at age 29. He understands the pattern: “Many founders have a crisis after selling their first company. They don’t know what to do, so they build another company just because they’re good at it.”
The reflex is to climb the same mountain again. It’s familiar. It’s comfortable. It’s also a trap.
The Post-Economic Mindset: When Money Stops Being the Primary Motivator
Shaan Puri offers a precise definition that cuts through the noise: “The definition of ‘post-economic’ isn’t that you have all the money you ever want. It’s that you no longer need to make decisions based on money as the primary motivator.”
This is the threshold that separates the two mountains. Not a net worth figure. Not a passive income number. It’s a psychological shift in how you evaluate opportunity.
Shaan has watched friends miss this shift entirely: “We have a bunch of friends—not going to name names—but they just keep putting points up on the scoreboard. They’ve already earned the last dollar they will ever spend in their life. And so now they’re trading great hours for useless dollars, which is such a wake-up call of a bad trade to make.”
Tim Ferriss admits he fell into this trap himself: “I passed my number and I felt like I needed more. I didn’t have a fixed number, but I felt like I needed more to have some degree of psychological safety and then everything will be okay. And then you realize that’s bullshit. Money solves money problems. You got plenty of work to do.”
The work he’s referring to isn’t business work. It’s the inner work of figuring out what you actually want.
Identity Diversification: Tim Ferriss’s Insurance Policy
If the trap is having your entire identity wrapped up in making money, the solution is obvious in theory but difficult in practice: build other sources of self-worth.
Tim Ferriss calls this “identity diversification.” He explains: “That’s why I think identity diversification and trying other things where you can feel good about yourself and chart progress—whether that’s piano, archery, any number of other things—is insurance against having a fixed-gear psychology.”
The key word is progress. You need activities where you can measure improvement, feel competent, and experience the satisfaction of getting better at something. Business provides this feeling. The question is whether you’ve built anything else that does.
Ferriss is intentional about his social environment: “I try to spend a lot of time around people—not just old friends—but spending time with some of the world’s best archers, swimmers, super high-level piano players who make next to no money, but who you can respect really, really, really deeply, who are fun to spend time with, who seem to have great lives and are more content than the rich people who are chasing the next phantom.”
The contrast matters. These are people who have mastered something, who command respect, and who are content—without being wealthy. Their existence is proof that the two mountains are different climbs.
The Eulogy Exercise: What Alex Hormozi Learned About Time Allocation
After his mother passed away, Alex Hormozi found himself writing her eulogy. The exercise forced a realization about time allocation that he couldn’t ignore.
“In writing her eulogy, it was interesting to see like what portion, if we had a pie chart, of this eulogy is going to be dedicated to her accomplishments? The vast majority of it was service and character.”
Then he applied that insight to himself: “Okay, well then if I were to apportion my time based on what my eulogy percentages would be, I would probably not have the same pie chart that I do now.”
Hormozi is unusually precise about his current allocation: “I’m probably like 70% work, 15 health, 15 marriage.” But he’s sensing a shift: “I think I would love to see a world where like 25 to 30% is business. I’d love to see what happens there. I think I’m feeling that transition right now.”
What makes this compelling is his vulnerability: “It’s the first time in my life where I’ve been open to having other priorities. I don’t know what they are.”
He doesn’t have the answers. He’s simply noticed that his pie chart doesn’t match his values.
What the Second Mountain Actually Looks Like
The second mountain isn’t a destination. It’s a different mode of climbing.
Jack Smith, after his $800 million exit from Vungle, chose a path that would confuse most entrepreneurs: “I wouldn’t say I’m retired because I’m working on stuff, but I’m not trying to build another billion-dollar company. I was successful early because I had a chip on my shoulder; I had something to prove. After Vungle sold, I realized I don’t have that chip anymore. I don’t need more money. Now, I’m motivated by impact—even if it’s just deeply impacting a few people.”
His conclusion was unconventional: “Setting up charities and a project in Portugal—a digital detox place for people to switch off from technology and be in nature. If it breaks even but heals people, that is success for me.”
Scott Galloway offers a frame for understanding this transition: “I knew a lot of people, let’s call them, that were up here for a little while. And when they came back down because they ran out of money or their fame evaporated, they became embittered. Whereas if you realize that life is about the climb up and down, and by the way, the climb down is the more interesting climb… the climb down is the climb towards meaning.”
The climb down. It’s a strange phrase. But it captures something true about what happens after the summit. You don’t stay at the top. The question is whether you descend toward meaning or fall into bitterness.
Beginning the Second Climb
Shaan Puri describes his career in two acts: “Beginning of career, 20s—I don’t even have the ability to get what I want. Regardless of what I wanted, I didn’t have the skill. So the first part of my career was just to actually figure out how to even get what you want.”
That’s the first mountain. Learning capability.
The second act is different: “Once you have the power to get whatever it is that you want, then the priority shifts to wanting the right shit. What do you actually want?”
The most important question now isn’t how do I get what I want? It’s what should I want?
Shaan has a practical answer: “Realizing that the decider of what to want isn’t money anymore. It may—maybe that was right when I was in my 20s, maybe it was wrong, but at least it no longer needs to be the case. And now pick a new word. Mine is ‘fun.’”
He’s applied this to his decision-making: “I told my brother-in-law, Sanjie Chopra, who is a successful real estate guy: ‘You’re throwing good hours after bad dollars.’ You’re trading life energy for money you don’t need. It has zero utility. Now, my criteria for a project isn’t ‘will it make money?’ but ‘is it fun and interesting?’”
The practical steps distill to this:
-
Do the eulogy exercise. What percentage of your eulogy would be about work? Does your time allocation match?
-
Calculate your “last dollar.” Have you already earned the last dollar you’ll ever spend? If so, you’re trading life energy for nothing.
-
Pick a new decision word. If money was your 20s filter, what’s your filter now? Shaan chose “fun.” What’s yours?
-
Build identity diversification. What activities give you a sense of progress and competence outside of business? If you can’t answer, you’re vulnerable.
The first mountain is about proving you can. The second mountain is about discovering what you should.
FAQ
What is the Second Mountain concept?
The Second Mountain comes from David Brooks’ book of the same name. In the MFM context, Sam Parr defines it as building beyond “just making your initial financial security number”—the transition from survival and achievement to meaning, legacy, and impact. Scott Galloway summarizes it as “the climb down towards meaning.”
When should you start thinking about the Second Mountain?
According to Shaan Puri, the shift happens when you’re “post-economic”—not that you have all the money you want, but that money no longer needs to be your primary decision-making factor. Tim Ferriss warns that waiting for a “number” often leads to goalpost-moving. Start when you have financial stability, not when you feel “done.”
What is the 2% Rule for financial security?
Michael Sonnenfeldt of Tiger 21 says: “If you can live on 2% of your assets or less, then you’re in a safety zone.” This means 200K/year spending. It’s a benchmark for when you’re financially secure enough to focus on second-mountain priorities without anxiety.
Can you pursue both mountains simultaneously?
Yes. Tim Ferriss advocates “identity diversification”—building skills and relationships outside of business while still working. Shaan mentions being “focused on thriving but also raising a good family and building a legacy.” The key is awareness and intentional time allocation.
Sources
Episodes
- Talking to Tim Ferriss about how to live a dope life — to-tim-ferriss)
- Behind The Scenes Of The Billionaires’ Mastermind (TIGER 21) | Michael Sonnenfeldt Interview — 21-sonnenfeldt)
- [[episodes/i_sold_a_company_for_800m_at_2|I Sold A Company For $800M At 29… What I’m Doing Now | Jack Smith Interview (#470)]] — smith-470)
- I Failed 12 Times Before Making My First Million (Here’s Every Failure) — 12-times)
- [[episodes/how_scott_galloway_turned__8m_|How Scott Galloway Turned 120M Through Investing]] — galloway-investing)
- How Alex Hormozi Gets Other People To Build His $100M+ Empire — hormozi-empire)
- 7 Brutal Questions for a $20B Founder — brutal-questions)