#business

Over my 20-year career as a founder, executive, operator, advisor, and investor in enterprise SaaS companies, I’ve been through a lot of ups and downs.

I’ve been an executive at two companies at inception (founding employee then CEO at one, and founder/CEO at BetterCloud). I was also an executive at one of the first cloud consulting companies just as they were getting started. At these companies we generated $100s of millions in ARR and hired thousands of people, including dozens of executives. We raised rounds from the best VCs in the world. But on the flipside, I’ve also been through a number of macro downturns, company pivots, existential moments of impending company failure, cash crunches, and terrible hires.

Recently, I’ve taken a step back from a day-to-day operating role. I’ve been spending more of my time advising early stage founders, many of whom are facing those very same challenges and situations for the first time.

To help shorten that learning curve, I’ve put together this “operating manual” with 50+ of my biggest lessons learned over the past two decades. It’s filled with personal anecdotes, actionable tips, and advice to help other founders avoid the same mistakes I made. I plan to apply all these learnings at my next company. Feel free to pick and choose whichever ones are most relevant for yours. (Note: These lessons are aimed toward early and growth stage companies.)

Not everyone will agree with my learnings or suggestions. As a member of several founder/CEO groups, I know people have strong opinions on how to run a company. That said, I’m still hoping this will resonate with readers. If each person just takes away one insight that will help them grow their business, then this was a success.

If there’s one general piece of advice that underpins everything, it’s:

Building is hard. Stay in the game to give yourself a chance to win.

The average time to an exit, if there ever is one, is over a decade. Be prepared for the grind. Yes, it’s going to suck at times, but it will get better.

Three critical things will help get you through the long haul: resilience, perseverance, and conviction. Ride it out. Continually learn, evolve, and move forward.

Keep going, keep growing.

Solo founders and small teams are shipping real products faster than ever.

Launching is the easy part. Once you're live, the hard part starts -- growth, monetization, security, stability — that's where most apps stall out or die.

We've scaled products to millions of users and hundreds of millions in revenue. Now we're building the tools we wish we had when we started.

Think of us as the cofounder you wish you had.

Prominent economists, including from Morgan Stanley and JPMorgan Chase, calculate that the AI buildup was directly responsible not for 92 percent or 39 percent of gains to the U.S. economy in 2025, but as little as zero.

It’s clear that the huge spending on AI is adding to the U.S. economy, but the available economic data doesn’t neatly capture its effects. The debating economists and the slippery data suggest that if the technology does start to reshape the economy, it may be challenging to detect and clearly measure. That may leave political and corporate leaders to choose the numbers that fit their preferred narratives on how AI is changing American life and work.

That’s because the $31 trillion in yearly U.S. gross domestic product, the widest measure of the economy, tallies only the final value of products and services produced domestically. Spending on imports and foreign made components is subtracted because it boosts the economies of other countries, not that of the United States.

Roughly three-quarters of the cost of an AI data center is for the computer gear and parts such as computer chips that go inside of it, technology analysts estimate. America’s AI champions, including the computer chip pioneer Nvidia, manufacture many of their products in Asia — despite efforts by the Biden and Trump administrations to reduce U.S. dependence on essential chips made overseas.

And some forecasters say that the U.S. government’s economic data is a poor measure of the impact of AI and that alternative calculations show the current boom is an even bigger boost to economic growth.

“This is a big deal, but not the be-all and end-all,” said Joseph Politano, an economic analyst who writes the Apricitas Economics newsletter. He calculates that AI-related spending contributed about 0.2 percentage points to the 2.2 percent U.S. economic growth last year.

The AI buildup is putting real money into the pockets of some Americans and U.S. businesses. Stock market gains from AI enthusiasm are plumping up Americans’ investment portfolios.

“The two engines of today’s economy are the AI ecosystem and wealthy consumers,” Richmond Fed President Tom Barkin said in a January speech.

Prominent economists, including from Morgan Stanley and JPMorgan Chase, calculate that the AI buildup was directly responsible not for 92 percent or 39 percent of gains to the U.S. economy in 2025, but as little as zero.

Prominent economists, including from Morgan Stanley and JPMorgan Chase, calculate that the AI buildup was directly responsible not for 92 percent or 39 percent of gains to the U.S. economy in 2025, but as little as zero.

Prominent economists, including from Morgan Stanley and JPMorgan Chase, calculate that the AI buildup was directly responsible not for 92 percent or 39 percent of gains to the U.S. economy in 2025, but as little as zero.

Prominent economists, including from Morgan Stanley and JPMorgan Chase, calculate that the AI buildup was directly responsible not for 92 percent or 39 percent of gains to the U.S. economy in 2025, but as little as zero.

Prominent economists, including from Morgan Stanley and JPMorgan Chase, calculate that the AI buildup was directly responsible not for 92 percent or 39 percent of gains to the U.S. economy in 2025, but as little as zero.

Prominent economists, including from Morgan Stanley and JPMorgan Chase, calculate that the AI buildup was directly responsible not for 92 percent or 39 percent of gains to the U.S. economy in 2025, but as little as zero.

Prominent economists, including from Morgan Stanley and JPMorgan Chase, calculate that the AI buildup was directly responsible not for 92 percent or 39 percent of gains to the U.S. economy in 2025, but as little as zero.

Prominent economists, including from Morgan Stanley and JPMorgan Chase, calculate that the AI buildup was directly responsible not for 92 percent or 39 percent of gains to the U.S. economy in 2025, but as little as zero.

Prominent economists, including from Morgan Stanley and JPMorgan Chase, calculate that the AI buildup was directly responsible not for 92 percent or 39 percent of gains to the U.S. economy in 2025, but as little as zero.

Prominent economists, including from Morgan Stanley and JPMorgan Chase, calculate that the AI buildup was directly responsible not for 92 percent or 39 percent of gains to the U.S. economy in 2025, but as little as zero.

Prominent economists, including from Morgan Stanley and JPMorgan Chase, calculate that the AI buildup was directly responsible not for 92 percent or 39 percent of gains to the U.S. economy in 2025, but as little as zero.

Prominent economists, including from Morgan Stanley and JPMorgan Chase, calculate that the AI buildup was directly responsible not for 92 percent or 39 percent of gains to the U.S. economy in 2025, but as little as zero.

Prominent economists, including from Morgan Stanley and JPMorgan Chase, calculate that the AI buildup was directly responsible not for 92 percent or 39 percent of gains to the U.S. economy in 2025, but as little as zero.

Prominent economists, including from Morgan Stanley and JPMorgan Chase, calculate that the AI buildup was directly responsible not for 92 percent or 39 percent of gains to the U.S. economy in 2025, but as little as zero.

Prominent economists, including from Morgan Stanley and JPMorgan Chase, calculate that the AI buildup was directly responsible not for 92 percent or 39 percent of gains to the U.S. economy in 2025, but as little as zero.

Prominent economists, including from Morgan Stanley and JPMorgan Chase, calculate that the AI buildup was directly responsible not for 92 percent or 39 percent of gains to the U.S. economy in 2025, but as little as zero.

Prominent economists, including from Morgan Stanley and JPMorgan Chase, calculate that the AI buildup was directly responsible not for 92 percent or 39 percent of gains to the U.S. economy in 2025, but as little as zero.