Most founders get one shot, but Mike has had six.
He has been CEO of six different venture-funded companies over the last thirty years in Silicon Valley. He has raised money from twelve different venture firms and taken three companies public. He has had exits that ended in nine figures, and one that ended in a fire sale. These days he sits on four boards and mentors first time CEOs. He just published a book called Failure Is An Option: Reflections of a Silicon Valley CEO, forty-four essays on what leadership actually looks like.
Venture capitalists get a portfolio. Back twenty or thirty companies, and most will fail, a few will do fine, and a couple will do very well. It is a good business model because it never depends on one bet. A founder does not get that luxury, which is what makes six tries at the same job such a strange kind of privilege. It means Mike got to make the same mistakes more than once, and eventually stop making some of them. Here is what six tries taught him.
Build a system to find out what is actually happening
Mike did not realise, when he first became a CEO, how hard it would be to know what was actually going on inside his own company. The bigger a company grows, the worse this gets. People hide bad news. Some are scared, some are political, some are simply bad communicators.
His mentor was Bill Campbell who was a college football coach who moved into business in his forties and, within a few years, was running sales and marketing at Apple. He went on to become CEO of Intuit and, eventually, the man Silicon Valley called “the coach”: Steve Jobs’s most trusted advisor, a quiet fixture in the rise of Google, and a mentor to founders far less famous than either. Mike was one of them. He met with Campbell once or twice a week for about ten years, and credits him, plainly, with the house he lives in today.
Campbell taught him the fix early. Do not trust your direct reports to tell you the truth, because either they do not know it or they will not say it. Cut through the management chain instead. Find the people at any level, in any role, who will actually tell you what is happening, and invest in them.
The formal half is a values driven culture, checked every quarter. Mike does not believe culture happens by accident. He picks a short list of values, things like integrity and relentless velocity, and bakes them into hiring and performance reviews.
Then he surveys the whole company every quarter to check whether it is actually living up to them, and shows every result to everyone, good or bad, no spin. The surveys have to be anonymous, because Mike has learned that even people who trust their CEO will still hold back the truth if they are not sure the anonymity is real.
Plans are useless, but planning is indispensable.
That is a Dwight Eisenhower line, originally about the battlefield, and Mike lives by it. A plan is obsolete the moment you write it down, because things move too fast. But refusing to plan at all creates chaos, jerking the company around with no explanation and no focus. The answer is a planning mindset, not a fixed plan.
Mike tracks company goals with a simple color system, checked every month. Green means a goal is on track.
Yellow and red mean it isn’t: yellow for goals that need attention, red for the ones seriously off course, and those are the colors Mike says he actually pays attention to, because they’re the ones you can still do something about.
Then there’s a fourth color most companies never bother with. Purple means the goal itself no longer makes sense.
Founders whiplash their own teams
The same instinct that makes a great early founder, always adjusting, always chasing the next opportunity, becomes a liability the moment a company scales. What feels like speed to the person at the top feels like chaos to everyone underneath them.
Mike learned this cost him real credibility with his own board. He once became convinced the company needed to pivot, and thought he had pre-sold the idea before the meeting. The board rejected it outright, not because the idea was bad, but because Mike had pivoted so many times before that they had stopped trusting his instincts.
It took him months to earn back the credibility he needed to make a pivot he had been right about the whole time.
Drinking the kool-aid
Mike’s first company spent years going nowhere. Then it started working, and a real acquisition offer landed on the table: forty million dollars, with room to negotiate up to something like sixty. Mike and his father controlled roughly half the company at the time, so in effect they were being offered thirty million for something that hadn’t gone very far yet.
Mike countered at two hundred million. The logic was borrowed, not earned: the company making the bid had recently gone public at an inflated valuation, so Mike figured his own company must be worth something comparable.
That is drinking the Kool-Aid, the term he uses for the mix of ego, overconfidence, and believing your own pitch too well. The deal died. The company sold six years later for meaningfully less money, and by then the cap table had shifted enough that Mike’s own ownership stake had shrunk considerably. He still thinks about it decades later.
Luck accounts for eighty to ninety percent of it
Mike does not think skill explains most outcomes. He puts the number at eighty to ninety percent luck, and backs it with two stories from opposite ends of the spectrum.
One company grew from nothing to a thirty million dollar run rate in under a year, then watched Congress kill the entire business model overnight with a single amendment to the Dodd-Frank Act. Pure bad luck, nothing to be done.
Another company was on the verge of going public when COVID slammed the window shut. Five separate attempts to sell, go public, or raise capital all failed over the following years, for reasons entirely outside Mike's control. Then, out of nowhere, an acquirer showed up and paid more than the IPO ever would have.
His advice to the CEOs he coaches follows directly from this: control your input, not the outcome, and expect luck to be doing more of the work than your ego wants to admit.
The debilitating win
The hardest founder to coach, in Mike's experience, is the one who got lucky once and cannot understand why it will not happen again.
One of his co-founders had been an early Netscape employee during the browser boom, then co-founded another company that also did well. His next venture, the one Mike was recruited to run as CEO, simply was not working, and the founder could not process it. He kept insisting he had done everything the same way as before.
Mike's private read was blunt: talented, yes, but the first two wins were luck, and struggling now is the normal experience, not the exception.
The loneliest job in silicon valley
After thirty years and six companies, Mike now spends much of his time coaching first time CEOs. When I asked him what the single biggest challenge is for the founders he works with today, his answer had nothing to do with markets or funding.
“All of them, to a lesser or greater extent, struggle with their mental health,” he said. “They feel an enormous amount of anxiety, there is lots of ups and downs, and they tie their identity to a great extent to whether the company is doing well or doing less well, and they have nobody to talk to. It’s a very isolating experience... very often they can’t talk to investors, because they feel if they show weakness or vulnerability, that’s uncomfortable and they might get penalized for it.”
The hardest part is that you bring it with you
I asked Mike how he balanced six companies against a family. He did not pretend there was an answer.
“These experiences put a lot of strain on families, at least in my experience,” he said. “I always prioritized family extremely highly, but I wasn’t able to do anything else, between the job and family, I didn’t have time for anything, including anything creative. There was no chance of that. But the hardest part is that you bring it with you. You’re always thinking about the business, always anxious about something. And when you’re with your family, you’re kind of half with them, but you’re half in your own head, still thinking about the business. I don’t think I ever got very good at that, through the years.”
Six companies is a lot of data. What it seems to have taught Mike is not a formula for guaranteeing success, since he does not believe one exists. What it taught him is where to put his attention. Build the systems that surface the truth. Hold a plan loosely enough to change it, without whiplashing the people counting on you. Do not confuse a hot streak with a law of physics. And when the outcome does not depend on you, focus on the parts that do.
Connect with Mike:
LinkedIn: https://www.linkedin.com/in/migrossman/
Book Failure is an Option: https://share.google/9DUEHB6596Eb1uXAa
Ways to Tune In:
Substack:
Spotify:
Apple Podcasts:
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
