Sponsored By
Introduction:
0-1 Series
If you missed it, a month ago I kicked off a series on all the firsts of Habits. Consider things like our first sale, how I found my co-founder, our first investor, attracting early employees, our first VC investor, and today will turn the clocks to where it all began…friends & family (F&F)
Paid Advertisement:
Find Your Financial Advisor with Habits!
Ever been curious if a financial advisor is right for you or your family? Download our app today and compare best-in-class professionals with any budget.
Also, did you know I’m available via text? You can reach me at (812) 805-0099.
Main Story:
Friends and Family (F&F)
I’ve been lucky to have a support system that most founders can only dream of but let’s be real, the whole friends & family thing isn’t always sunshine and cap tables for everyone.
via GIPHY
At some point, family dinners start feeling like investor pitches. Your friends become unpaid beta testers. Your partner turns into your on-call therapist (with zero PTO), and that one neighbor insists they "totally get it" because they sold lemonade in middle school — cool, Phil.
So yeah… let’s get into it.
The F&F 101
So here’s the deal — there are two camps when it comes to Friends & Family (F&F) fundraising or getting them involved.
(1) Camp "Keep Them Out of It": You’re low-key (or high-key) terrified this thing might crash and burn, so the last thing you want is for people you love to lose money on you.
(2) Camp "Let’s Get Rich Together": You fully believe you’re building the next billion-dollar company, and if anyone’s gonna get rich off your blood, sweat, and tears — it better be the people who believed in you first.
Some investors will say F&F money makes your cap table messy. Others will side-eye you if your F&F don’t invest — like, “If your own people won’t back you, why should we?”
What I did
For perspective — I didn’t actually raise any capital from Friends & Family. But what I did get were commitments. The kind that gave me enough confidence and momentum to go out and raise from angels.
I found a place to live for $600 a month (shoutout to living lean). I had couches to crash on anytime I needed to travel. And when we finally raised our first $250k, I’d argue maybe $75k of that came from mentors, early adopters, and a few close friends — but not a lot from the classic “Friends & Family” pool.
Email sent to F&F in June of 2023
Instead, I turned to them for something even more valuable — to be our first users. And wow, did they show up. They blew every expectation I had out of the water.
And let me tell you — there is nothing cooler than getting a text from a random high school classmate, an old coworker, or a best friend that says,
“This Habits thing is going to take off — I’m so impressed.”
You can’t buy that kind of support. You can’t fake it either.
The Embarrassing Truth
If I’m being really honest — when I left JPM, I kinda lied to a lot of my friends and family.
I told them I was taking this fancy new VC gig with a cool rotational program. (Spoiler: it was Techstars. There was no rotational program. LOL.)
The truth? I wanted to start what eventually became Habits — but I had absolutely no clue what I was doing.
And let me tell you, you can spend years thinking you’re smart (5–6 years counts as a career, right?). You can think you’re crushing it in your job, rising fast, winning awards, whatever. But nothing humbles you faster than sitting alone on a random Sunday, staring at a blank Google Doc, realizing you just quit a job that thousands, maybe tens of thousands, of people would kill for… and wondering if you just made the dumbest mistake of your life.
Because that VC gig? It was a three-month contract that, in total, was gonna pay me less than one of my bi-weekly paychecks from the bank.
I remember one day, driving my sister back to her apartment in Chicago, and I sorta let it slip that I was working on “something”—super vague—and casually asked her what she thought of the name Habits.
She told me to f*ing go for it**.
But she was also blunt — she said, “Look, I’m in grad school. I don’t have money to help you.”
What she didn’t realize is that just hearing her say “go for it” did more for me than I can ever explain.
The Takeaway?
This might sound strange…but you need to be comfortable asking for help or at least allowing people to help you. For example, here is a random list of ways my F&F have come through.
One referred a former roommate who has now been an employee at Habits for over two years.
A college friend allowed me to live in his rental property for pennies on the dollar.
A cousin has over 25+ referrals for this blog.
A friend I lost touch with over the years invested $15,000 the moment they heard I was building a startup.
My buddy and his fiancee are probably my #1 supporter on LinkedIn.
Roughly 50% of our cap table is a result of warm introductions.
My immediate family for being my biggest cheerleaders and advocates in their daily lives.
So to those of you still reading, thank you too. Each day is a dream come true. It’s stressful, it’s hard, but you all make it worth it. My email is jack@usehabits.com, don’t hesitate to let me know how I can return the favor and support you (also if you need a financial advisor, I gotchu fam!).
What’s Coming Next?
Next week I’m going to share anecdotes from the thousands of families that I’ve met through Habits. Why? Well I think we all like to get a inside peek of how others spend their money, what they make, and how they approach their finances.
Sharing Is Caring
Do me a favor, if you enjoy this, share it with a friend!
