30 Lessons I Learned from 11 Years in VC and Startups – Money Savvy

After more than a decade, I left CRCM Ventures last month. Over the past 11 years, I spent 7 years running a VC firm and 4 years running an ecommerce business. CRCM was my home — starting when I was in business school and continuing throughout my venture capital and startup journey. It’s been an incredible, life-changing ride, and I’m deeply grateful to my colleagues, limited partners, advisors, and the founders I worked with over the years.

As I step into a brief period of unemployment (or as I like to call it, “career sabbatical with free childcare benefits”), I plan to spend more time with my daughters, more time at Bay Area climbing gyms, and more evenings playing pickup basketball. I also plan to explore what’s next for me professionally — though, full disclosure, I tried the whole “retirement” thing for a couple of weeks, and I hated it. So for now, I’m advising a handful of startups and venture funds while figuring out my next move.

Looking back on the past decade, I’ve accumulated a fair number of lessons — some learned the hard way, some picked up from great mentors, and some from falling flat on my face (literally, in rock climbing). In a series of brutally honest, unfiltered posts, I’ll share my takeaways with founders, aspiring VCs, and anyone trying to carve out a fulfilling career. Hopefully, some of this will resonate — or at least save you from a few of my mistakes.

10 Lessons on Family, Relationships, and Health

1. Sleep is a cheat code for life. We make one or two truly important decisions a day — being well-rested makes sure they aren’t dumb ones. Sleep has one of the highest correlations with good health and life expectancy. This is still something I struggle with, mostly because Netflix exists and my daughters think 8:00am is “sleeping in.” Pro tip: Coffee is not a substitute for sleep. It’s just a socially acceptable way to act like a zombie.
2. Exercise is non-negotiable. Everyone knows this, but consistency is the hard part. What worked for me: accountability partners (my 7-year-old daughter in rock climbing, my weekly pickup basketball crew, my brother in weight lifting).
3. A strong family support system lets you take bigger risks. My wife’s stable job in big tech/consulting allowed me to pursue higher-risk, higher-reward opportunities. Volatility is great for investing, but stability is best for a home.
4. Have a hobby that isn’t tied to money. Something just for you — no expectations, no financial gain, just pure enjoyment. For me, it’s basketball and rock climbing. Bonus: When you’re clinging to a wall by your fingertips, you can’t check emails.
5. It’s never too late to start something new. I started learning piano at 35 (with my daughter who constantly corrects my sight-reading), climbing at 35 (see: mid-life crisis), and snowboarding at 36 (see: mid-life ER visits). Life’s short — pick up that hobby or that thing you always wanted to try. Worst case, you’ll have a great story.
6. Some things you enjoy much more when you are young. In my 20s I used to spend 2 hours lifting weights, follow it with 2 hours of basketball, and eat an entire rotisserie chicken for dinner. I used to travel much more and take red-eye flights with no issues. In my late 30s some of these things are much harder to achieve. Despite how hard we work and how devoted we are to our careers, we should still take time to do those things we love when we are young. Driving a fancy sports car at an old age (after you’ve “made it”) is not going to be as enjoyable as doing it when you are young.
7. Create time to slow down and think. Some of my best ideas came not from grinding but from taking a step back. We get so busy with work and family life that we forget to ask, “Wait, why am I doing this?” Pro tip: shower thoughts count.
8. Invest in friendships. A close group of friends will keep you sane. Build relationships you can rely on — the true ones are those who’ll laugh at your jokes from years ago and still answer your 2 AM texts.
9. Stop worrying about what others think. The older I got, the more I realized other people’s opinion of you really matters a lot less than you think. We should do things for ourselves and those we care about, and not to impress others.
10. Success isn’t just career and money. Health, family, and friendships matter just as much, if not more. Also, Call your parents. They won’t always be around, and they are the only people who still think your startup idea is brilliant

10 Career Lessons

1. Don’t sell your time; own something instead. We were taught to chase stable jobs, but no one (besides famous musicians and athletes) became wealthy via salary. Wealth comes from owning assets that appreciate over time. When possible, trade salary for equity and a share in the upside.
2. Not all advice is good advice. The trick isn’t getting advice — it’s knowing whose advice to take. For every Warren Buffet, there’s a guy on LinkedIn telling you to “hustle 25/8” while selling crypto courses.
3. Fishing in the right pond > Being a great fisherman. Picking the right industry is more important than picking the right company. The early 2010s mobile/social wave made a lot of VCs look like geniuses. Market cycles matter.
4. Prepare, then get lucky. Luck plays a big role, but you can increase your odds by being ready. You can do this by being in the right industry, working with the right people, have a meaningful share in the upside, and stay for the long game.
5. Know when to pivot. Most startups (and careers) don’t go as planned. The ones that survive pivot early and decisively. It’s not easy to admit when you’re wrong, and it’s even harder to course-correct and move on. The best leaders I’ve seen are those who are willing to make the difficult decision to pivot, even when it means significant changes to their team and product.
6. Confidence is a superpower. I grew up in an immigrant household where humility was emphasized, but confidence was never taught. Turns out, the most successful people aren’t always the smartest — but they are often the most confident.
7. Learn to sell. Whether it’s a product, an idea, or yourself — sales skills are everything. Master storytelling.
8. Find great mentors and leaders. The right mentor can change your life. Traits of a great leader: (a) shared values, (b) they care about you, (c) mutual trust, (d) they’re really good at what they do. Avoid mentors who say, “I’ll help you — for 10% equity“
9. Build your network. No one succeeds alone. Surround yourself with the right people.
10. Always ask. The worst they can say is no. And a “no” today might be a “yes” in the future.

10 Wealth Lessons

1. Don’t break the law. The fastest way to lose everything is to get permanently knocked out of the game.
2. Get financially literate. You’d be surprised how many Ivy League grads have no idea what to do with their money. Wealthy people save, invest, and make their money work for them. Your money is the biggest tool to acquire more money.
3. Wealth comes in big moments, not steady paychecks. Life-changing money happens through rare events — exits, IPOs, big bets.
4. Concentration builds wealth, diversification preserves it. Diversification is for the already rich. No one got wealthy by splitting their bets. They got rich by going all-in on something they believed in.
   • Be patient. The right opportunity is worth waiting for.
   • Don’t get knocked out. Even with a concentrated bet, keep a rainy-day fund. (Because ramen gets old fast)
5. Maximize time, not just money. Beyond a certain point, money has diminishing returns. Optimize for freedom.
6. Beating the S&P is hard. Most people should just buy the index and chill.
7. Live below your means. Just because you can afford it doesn’t mean you should buy it. Simplicity is underrated.
8. Understand taxes. From tax-loss harvesting to step-up basis, knowing tax strategy keeps more money in your pocket.
9. Teach your kids financial literacy. It’s one of the best gifts you can give them. Bonus: They’ll stop asking for a pony
10. Own some Bitcoin. Just do it.

Final Note: If you take away one thing from this, let it be lesson #11 from the Family section: Call your parents. They’re your earliest investors, after all — and unlike VCs, they’ll never ask for a return.