What if the six companies you sold had less to do with your talent than with the two people who told you to go?
Mike Grossman has run six venture-funded technology companies over thirty years, every one of which was acquired. He now sits on four boards, informally coaches close to ten first-time CEOs, and wrote Failure Is An Option: Reflections of a Silicon Valley CEO.
The two relationships he credits most sit on either side of his life. Bill Campbell, the Silicon Valley coach who led Intuit and advised Apple and Google, met with him weekly for a decade and gave him the advice that saved a company sale. And his wife, whom he met by accident in Melbourne, is the reason he became a full-time entrepreneur at all.
His career centers on venture-funded early-stage software.
He serves customers, employees, and shareholders.
The aspiration is "best company I've ever worked at."
He knew as a teenager he wanted to build things.
His first company sold art wear T-shirts in his mid-20s.
It held the exclusive license to Norman Rockwell's art.
He spent ten years as a full-time entrepreneur.
After an acquisition, his co-founders were unavailable.
He was recruited in as CEO of a pre-revenue company.
An entrepreneur builds momentum out of nothing.
A recruited CEO inherits momentum built over years.
The CEO role leans toward culture and priorities.
Early on, building something new was the thrill.
Now developing people's careers motivates him more.
That shift would have surprised him decades ago.
His last company sold for many hundreds of millions.
The outcome followed from the culture, not the reverse.
Customer satisfaction and employee passion were both high.
Across six companies, results varied widely.
Industries and circumstances were very different.
Every one had a strong values-driven culture.
He coaches close to ten first-time CEOs.
He sits on four boards and still brainstorms ideas.
He expects to run at least one more company.
They met when Mike worked at Intuit, where Bill was CEO.
Bill became his coach at his first tech company.
They met one to two times a week for ten years.
An acquisition opportunity arrived for the company.
A contract he signed a year earlier held an ambiguous clause.
Read the wrong way, it blocked the sale entirely.
Bill advised confronting the issue head-on.
The board had told him not to.
He convinced the counterparty to release the agreement.
Dun & Bradstreet spotted the clause and flagged a problem.
Mike could answer that the contract no longer existed.
That is how the company sold and how he bought his house.
A roommate spotted a poster for an Australian law firm.
He was assigned Brisbane, then switched to Melbourne.
He met his wife within a week of arriving.
He was in Boston while she was in Melbourne.
There was no email, text, Zoom, or FaceTime then.
They kept it going and got married.
His wife's pregnancy forced the entrepreneurship question.
She said to start the company and offered to fund insurance.
He left his job the same day she went into labor.
Luck plays an enormous role in outcomes.
People focus too heavily on results.
You control the effort, not the result.
"The reason the outcome was so good is because of all of these other pieces, and that's what I'm most proud of." - Mike Grossman
"Much of what I do as a CEO, I learned from Bill. The reason I'm sitting in this house that I'm in as I talk to you is thanks to advice that Bill gave me at a very critical juncture." - Mike Grossman
"Everything about my life now really is connected to that largely random event of meeting her in Melbourne." - Mike Grossman
"People focus too much on results, and really, we don't have that much control over results. We have a lot of control over the input, over the effort we make. But what ends up happening is often unpredictable." - Mike Grossman
Website: https://www.failureisanoption.com
LinkedIn: https://www.linkedin.com/in/migrossman
Email: mikegrossman86@gmail.com
Book: Failure Is An Option: Reflections of a Silicon Valley CEO
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