The Path from Founder to Investor
Everyone talks about how HARD it is being a founder.
The sleepless nights...the constant self-doubt...the emotional rollercoaster of fundraising...the endless stream of fires to put out...
But honestly? That's not even the worst part.
The REAL torture—for me at least—was always having to focus on ONE. SINGLE. THING.
Day after day, year after year—while watching 100 other exciting opportunities pass you by.
It's like being handcuffed to the same project...while the rest of the world is having a party without you.
And if you're venture-backed? Forget about it.
You've basically signed a blood oath to give your entire existence to this ONE thing.
✅ Pro tip: Don't raise VC money if you're not ready to be ALL IN for years.
THIS is exactly why investors have it better.
Sure, the investor life has other perks:
- It's easier than building
- More predictable than the startup grind
- Actually lets you have a life
But the REAL benefit?
You get to stick your hands in ALL the cookie jars.
Instead of being chained to one business...
Your job is literally to: - Meet brilliant founders
- Learn about new markets
- Help solve interesting problems
- Get paid to be curious
Does it replace the high of building something from nothing? Hell no.
Nothing beats that founder rush. But for an ADHD generalist like me, being able to play in multiple sandboxes is pretty damn sweet.
That's why at The Family Fund, we're not just building a firm. We're building a COMMUNITY of founder-investors.
We brought in 67 founder LPs in Fund I, and we'll have 100 for Fund II.
Why? Because founders make the best damn investors. Period.
They just need the right training—and the right community around them.
So after 20+ years of building and 4 years of "professional" investing (whatever the hell that means), let me share the 10 biggest lessons I learned making the switch from founder to founder-investor.
👇 10 Lessons From a Founder-Turned-Investor:
1. Every Great Deal Has Multiple Legit Reasons to Not Do It
We've invested in some absolute beasts: Ghost, Bloom, Superpower...
And every single one had "red flags" that made smart people nervous.
Here's the thing about investing…
If EVERYONE loves the deal, you're probably overpaying.
The magic happens when you see something others don't.
2. "Industry Experts" Are Often Wrong
Look...we've got 60+ founder LPs backing The Family Fund. Smart MFers who've built MASSIVE brands.
But even THEY get it wrong sometimes.
Why? Because they judge new opportunities through the lens of how THEY did it.
And that approach is usually outdated by the time they're "experts".
The key is to collect insights from everyone around you, but make your own damn decisions based on your unique analysis, convictions, and foresight.
3. Pattern Recognition Is Just Table Stakes
Yes, you need to spot similarities between: - What worked before
- What's working now
- What might work next
Because pattern recognition helps you: - Conduct signal filtering with speed
- Execute effective judgment under uncertainty
- Maintain a competitive edge in spotting emerging trends before they become obvious (e.g., consumer biohacking in 2017, AI infrastructure in 2022, GLP-1 crossover brands in 2024)
But if that's ALL you do, you'll miss the next Airbnb, Figma, or Happy Dad.
Those companies BROKE patterns.
Investors who over-rely on pattern recognition experience: - Survivorship bias (you remember what worked, leading to overconfidence in false positives)
- Blindness to novelty (breakthroughs often break the mold)
- Bias amplification and the execution of stale playbooks
Use pattern recognition as a compass, not handcuffs.
4. Proprietary Deal Flow > Everything
Most investors will flex their:
- MBA
- Past exits
- "Thought leadership"
But none of that matters if you're not seeing the best deals.
It's like Gordon Ramsay cooking with ingredients from a gas station.
5. The Best Time to Invest? When Everyone's Scared
When fundraising gets tough: - Deals get less competitive
- Valuations come down
- Smart money makes MOVES
Remember: You make money on the BUY, not the sell (but you gotta' be sure you can sell…)
6. Effective Portfolio Construction Is Essential
✅ Here's how pro early-stage firms think:
"70% of our investments might fail...but 1-2 huge wins will carry the fund."
❌ Here's how amateur angels think:
"I'll put all my money in 1-2 deals and pray."
Then they're shocked when they lose it all.
A diversified strategy that is built around risk is essential to producing solid returns.
If you're an angel and want to invest $100K, put $10K into 10 deals with the same firm at the same stage.
That's what pros do.
7. Missing Good Deals > Making Bad Ones
Real talk: We've passed on deals that turned into monsters. And yeah, it stings.
But you know what hurts worse?
Investing in companies you regret investing in.
If you have great access, you're either going to miss picking great deals from time to time, or you're going to invest in way too many companies you shouldn't have.
8. Values-Driven Decision Making Will Save You from Hell
We've walked away from deals that could've made us bank…
Because: - The founders were toxic, and/or
- The product was BS with little to no efficacy
Missing killer deals HURTS.
But here's the thing about saying "NO" to deals:
It's better to miss out for the RIGHT reasons than to invest for the WRONG ones.
Because at the end of the day, your values are the only thing keeping you from becoming just another soulless money chaser.
A VC firm without strong values is like a ship without a rudder.
Sure, you might catch some favorable winds...and float in the right direction for a while...
But eventually? You're gonna crash into something ugly.
And let's be real...
Who actually wants to get rich selling garbage to people who don't know better? (Besides half of the "gurus" on your Instagram feed)
9. If You Need to Run Their Business, You Picked Wrong
I'm a founder at heart.
I LOVE getting my hands dirty with marketing and operations.
But if a company NEEDS that from their investor?
You probably shouldn't have invested.
Great founders figure shit out themselves.
10. Be a Likeable Human
Shocking revelation: People prefer doing deals with people they LIKE.
All the fancy analysis in the world won't save you if you're just not fun to work with.
⭐️ BONUS LESSON:
The best deals rarely come from pitch decks—they come from relationships.
That's why being a good human > being a smart investor. | 
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