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0-1
For the next 4-6 weeks, I’m laying it all out—the firsts that built Habits. First sale, first hire, first MVP, first angel check. And, of course, the first time we completely screwed up (which happened a lot). No fluff, no startup fairy tales—just the raw, messy reality of figuring it out as we go. If you’ve ever wondered what it really takes to build something from scratch, keep reading.
Our First Sale
Here is the first, and arguably only lesson you need to know about startups…sales solves a lot of problems. Need to raise a round? Need to attract top talent? Need to open an office? Need the biggest booth at the annual industry conference?
Every single one of those are solved with sales. It either gets money through the door or creates a sense of FOMO. Because one day you’re going to blink and your pipeline is going to explode.
We had 29 inbound demo requests in January ‘25
If you told me in April ‘22 that we’d add ~$250k demo requests in January of ‘25, I’d ask what you’re smoking. Oh and by the way, that doesn’t include the 5 LOIs we’re securing that will result in $2M+ in ARR.
DM’s For Days
I left JPM’s Private Banking FIG team around April of 2022. Months later I was email-introducing families with financial advisors. No website. No HubSpot demo request forms. No team. Nada. So I promise, if I can do cold outreach with nothing to show for it, you can too.
Cold outreach via LinkedIn to a financial advisor in August ‘22
Oh…and this financial advisor eventually responded years later.
Their follow up (last week) after seeing the announcement of our raise
I’ll drop some additional LinkedIn DM screenshots at the bottom of this post for your entertainment.
So how did we go 0-1? I spent hours every day, every night, every time I sat to take a sh*t, every Uber ride, every flight, any moment I could spare…I sent a connection request and immediately followed up with a DM to financial advisors.
0-1 doesn’t take talent. It takes effort.
Sales Deck
I’m a big believer in the whole “how you do anything is how you do everything.” So your sales deck needs to be impressive. Especially if your product or service is early on. Bear in mind, your first will be sh*t and cringy, but it’ll get better with time and feedback. Here is my general approach:
Cover Slide (include a clever one liner)
What You Do
Why You Do It
Industry Data & Research
Existing Solutions (and why they suck)
Demo
Unfair Advantage or Secret Sauce
Evidence or Traction (why you win)
Competitors (how you’re different and why you’re better)
Pricing
Next Steps & Onboarding
WOW factor (something that blows their socks off)
Contact or Appendix
Simply put, instead of thinking “How do I get them to say yes?” you should ask yourself “How do I make it impossible for them to say no?”
Refundable Deposit
We eventually got to a point where I would send families a PDF file with the LinkedIns of the financial advisors I knew personally. And at this point we weren’t earning revenue.
Because I was scared. And it feels so silly looking back. I was legit scared to make the ask. But by the summer of 2023 my co-founder and I asked the financial advisors (on that PDF) to pay us $750 as a refundable deposit.
In our eyes it was high value at low risk. At any point they could ask for their money back. But we knew we could deliver.
First Sale
We managed to get 15-20 financial advisors to pay us the $750 deposit. But by January of 2024, literally a year ago, we said “alright if you want to stay on the platform (which at the time was a Squarespace website) it’s gonna cost you thousands.”
We didn’t give a single refund. Now we charge 10x that original price. Minimal churn, high adoption, better engagement, and helping more families than ever find a financial advisor.
0-1 is all about moving an inch each day. And eventually you’ll be moving miles each day. So don’t overthink it, get out there, and don’t be afraid to stand on a corner with a sign that says “Ask me about my startup” like I did in Boston on numerous occasions.
More DM’s For Your Entertainment
Got creative with my DM’s and targeted people I engaged with on LinkedIn
Sometimes people will take your call, you just gotta shoot your shot
People will ignore you, but don’t give up
This advisor ghosted my a** for years and now they’re interested since a friend referred it to them. Just goes to show you, cold outreach just doesn’t work on some people.
What’s Coming Next?
Next week I’ll get into finding my co-founder, attracting our first employees, identifying our first legal team, and trying my best to show how one day your begging people to join…to a couple years later where people are begging YOU to join YOUR cause.
Sharing Is Caring
Do me a favor, if you enjoy this, share it with a friend!
Find Your Financial Advisor
If you’re somebody on the sidelines or are not sure if a financial advisor makes sense for you or your family, just shoot me an email at jack@usehabits.com.
Or… visit our website to learn how we’ve made it easy for you to figure out on your own.
