The Advantage #26: What I Really Made on the Freshly Sale, Why the Trophies Are a Trap, and Turning a $20 AI Into Your Executive Coach
What a big exit is really worth, why the trophies are a trap, and a $20 executive coach.
Welcome Note
Thanks for reading the twenty-sixth issue of The Advantage. Three sections this week, loosely tied together by money and mastery: what a big exit is really worth, why chasing the trophies is a trap, and a nearly free way to get better at your own job.
First, in What I'm Working On, I went on Moneywise and got more specific about the Freshly economics than I ever have, including the exact amount I took home. Then the watch is Chamath Palihapitiya on why the cars, the watches, and the planes are a distraction, and why founders build to create something, not to flex. And the Practical Edge is a new way I am using AI, as a brutally honest executive coach that reviews how I actually showed up, for the price of a subscription. Let's get into it.
WHAT I'M WORKING ON
The Freshly Economics I Have Never Shared
Moneywise · with Daniel Berk
I just recorded an episode of Moneywise with Daniel Berk, and we went deeper into the economics of the Freshly journey than I ever have publicly. From $15 in my bank account, a personally guaranteed 20-year lease, and a million-dollar judgment against me, to a $1.5 billion sale to Nestlé, to Nestlé shutting the whole thing down. It is the most specific I have ever been about the money. The exact amount I took home from Freshly. What a $100 million wire actually feels like. The number you can retire on versus the number I am still going for. And the levels of wealth, from my perspective.
One fun twist. Daniel is an entrepreneur building in the media space who runs Moneywise, and we flipped the mic and interviewed him for The Advantage podcast, out in the next few weeks. This one is him interviewing me.
This week's Worth Watching is a 13-minute clip from Chamath Palihapitiya on why the trappings of success are a trap. I'll be honest about the messenger. Chamath has spent years on the other side of this exact message, the planes, the $2,000 sweaters, the very flexing he's now warning against. That's what makes the clip land harder, not softer. This is a guy who speed ran all of it, bought the cars, checked the NBA owner box, checked the plane box, and came out the far side telling you it was a distraction. On this one, he's right, and he's saying the thing I say about startups all the time.
WHAT I LOVED ABOUT IT:
The Instagram version of success, the cars, the watches, the private planes, gets clicks. It's not why you start a company. You start a company because you want to build. You want to put something into the world that doesn't exist yet. The trophies are a scoreboard someone else handed you, and the moment you start playing for it, you've lost the plot.
Chamath's watch story is the whole lesson in miniature. He bought one, then another, then needed a winder, then a jeweler, then insurance, then off-site storage. Every possession added complexity that had nothing to do with anything that mattered. His line for it is that the more you buy, the more those things own you. The more distracted he got, the less successful he became.
What makes it more than a rich-guy lecture is the honesty about ego. He walks through the SPAC run and admits the failure was architected by how he saw himself in the success. A million followers and a flood of free money went to his head, and he mistook a moment for a skill. That's the part every founder should sit with, because it's hardest to see your own ego exactly when things are working.
THE LINE THAT STUCK
"The more things that you buy, the more that those things will eventually own you."
MY 20-SECOND RECAP
if you don't have the full 13 minutes
→The trophies are someone else's scoreboard. Cars, watches, planes. That's living by a definition of success you didn't choose. For founders, the Instagram version of winning is a distraction from the only scoreboard that counts, which is whether you built the thing.
→Possessions own you. The watch spiral says it all. Winders, jewelers, insurance, storage. Every status object adds complexity that pulls time away from the work and quietly makes you worse at it.
→The greats buy time, not status. Chamath's read on Elon, Jordan, Kobe, and Taylor Swift is that they use money to free up time for excellence, not to signal it. Optimize for time on the thing that matters and let the rest go.
→Success and failure are sisters. He's refreshingly honest that his crash was seeded by his own ego during the win. Watch yourself hardest when the stock is up and people suddenly care what you think.
→Build because it feels like a game. The thread he kept true to his whole life is that he loves games, risk, and solving problems. Building a company is a game you actually want to play. That's the point. The money is a lagging indicator, not the goal.
PRO MOVE
Run his litmus test this week. At the end of a workday, do you walk to the people waiting for you at 6 pm as your full self, or do you need an hour to decompress first? If the work energizes you for the rest of your life, you're building the right thing. If it whittles you down, that's the signal.
Here is a new way I have been using AI that I think is worth a try. Not for the work in front of you, but on you and how you do your job. I use ChatGPT and Claude as my executive coach.
WHY IT WORKS
A great executive coach costs hundreds of dollars an hour and has a waitlist, so most founders get one years too late, if ever. This does the same job for close to free on the platform you already pay for. It is on call at 11 pm before the board meeting, and if you feed it the actual transcript, it is reacting to how you really showed up, not your memory of it. Because I am the one who asked to be reviewed, I am wide open to the feedback, the same way you are with a coach you hired to tell you the truth.
THE DATA SUPPORTS IT
The ICF and PwC Global Coaching Study found organizations that tracked it reported a median return of 5 to 7 times their coaching investment, and a widely cited MetrixGlobal study at a Fortune 500 company measured a 529% ROI, rising to 788% with retention. Feedback is one of the most studied levers in management: the landmark Kluger and DeNisi meta-analysis, 607 effect sizes across more than 23,000 observations, found it improved performance most when tied to a clear standard. That standard is exactly what you build into the prompt.
HOW I USE IT
The unlock is transcripts. I record almost everything and feed it in. In interviews, the obvious read is on the candidate. The one I had been overlooking is the read on me: did I talk too much, sell instead of dig, let a weak answer slide? I do the same before and after board meetings, for every one-on-one, group meeting, sales call, and the rest. If you paid a coach to do all this, it would be hundreds of thousands a year. For $20 ($100 if you go max, which I strongly recommend), a little organization and process, and you have a 24/7 coach.
The power is not the question you ask. It is the setup you build before you ask it. A weak prompt says "review me as a top CEO." A strong one gives the model the context and the standard to judge you against, so you get real feedback instead of flattery. Here is how I build it:
→Load your context. Company stage, who is in the room, your history with them, and your own goals ("I tend to talk too much and rush to solutions"). The more you use it, the more it learns. But you always want to keep a tight context window in the skill.
→Define the standard, and borrow a proven one. Do not let it guess what good looks like. Point it at an established framework, and if you are not sure which, ask it to research the best one for your situation first. So a little homework on your part goes a long way. For hiring, grade against Topgrading or the scorecard method from Who: The A Method for Hiring. For one-on-ones and feedback, Radical Candor or the SBI model from the Center for Creative Leadership. For board meetings, the playbook in Startup Boards. A named standard turns vague reactions into real feedback. There are lots out there. Choose the one for you.
→Make it cite the transcript. Demand specific quotes and moments, not impressions.
→Force a priority. Ask for the single highest-leverage change, not a list of twelve.
→License candor. Tell it you want the hard version. Models flatter by default, and you have to override that on purpose.
Then save it. Once the setup earns its keep, turn it into a reusable skill so every future transcript gets the same rigorous read and it starts to learn your goals and track whether you are actually improving. That is the moment it stops being a prompt and becomes a coach that knows you. It is also what finally made the $100 tier worth it for me.
Thanks for reading.
Mike Wystrach
Founder · Operator · Investor
→ Know a founder chasing the image instead of building the thing? Forward this to them.