^{Sponsored Ad}

Training The Street

Training The Street is the industry-standard training used by analysts at banks like JPMorgan, Goldman, Morgan Stanley, and Evercore. They’ve helped thousands of students and career-changers break into IB, PE, VC, and beyond.

They’ve got you covered with: a full Investment Banking Bundle, discounted 25% off for my readers (code: HABITS25)

Training The Street is where the pros go to prep.

^{Top Content From Last Week}

Put Yourself Out There

It’s actually crazy to think that any day now I’ll cross 10,000 followers on LinkedIn.

In 2021, I didn’t directly say this, but a former banking colleague reminded me I commonly said “the people who post on LinkedIn are the absolute worst.”

^{Main Story:}

I Pitch VCs Every Quarter

Everybody LOVES to talk about raising from venture capital funds.

You hear it at every happy hour, every podcast, every LinkedIn post. But here’s the thing I’ve learned after a few years in the game: most people who have never been a founder or a key decision-maker at a fund don’t actually understand how it works…no matter how confidently they talk about it.

The truth? It’s all about storytelling.

Yes, business model matters. Big markets matter. Engagement and traction matter. But none of it matters if you can’t tell the right story to the right person at the right time.

And relationships drive all of it. That’s why I think anyone who preaches absolutes—“always bootstrap” or “raise as much as possible”—is full of sh*t. Absolutes are rarely the right answer in business. The reality is fundraising is all about how you manage the grey.

What Investors Really Ask

Every meeting eventually circles around the same set of questions:

• Why now?

• What’s your unfair advantage?

• What do you know that nobody else does?

That’s the checklist. Everything else: your TikTok following, your shiny deck, your awesome looking team, your fancy demo or financial model…barely moves the needle.

Pitch decks get you into the room. Warm intros help. But at the end of the day, it’s not about the numbers. It’s about whether your story resonates. And that usually comes down to something personal: maybe they’ve lived your problem, maybe they’ve invested in something adjacent, maybe they just like the way you carry conviction.

Especially early on, investors don’t invest in metrics. They invest in stories they believe in and the people behind them.

The Six-Month Lie

A couple months back, I wrote that Habits had six months of runway. That wasn’t exactly true.

What I meant is that Veera (my co-founder) and I think in six-month windows. That’s how we measure health and make decisions. Not because we’re reckless, but because at our stage, anything beyond six months is basically a hallucination.

• One week, you realize you need to hire a data engineer.

• The next, an enterprise client falls through.

• The next day, three more sign up for trials.

It’s chaos. Because one day we’re watching every penny leave our bank account, and other days we randomly get an influx of $$$ because something worked out.

So when it comes to fundraising, it’s no different. But the tricky part, investors care about different things. Some want to know the specifics of your MoM growth rate for sh*t and giggles, others swear by a specific growth or traction formula, while the rest just say to themselves “do they got something here???”

The most honest founders admit they only have visibility six months out. Everything else is a guess. The tricky part is knowing what to share, expand upon, and articulate to investors.

Where Habits Is Right Now

We’re past the “is this even real?” stage.

• The product works.

• Users are engaged.

• Pain points on both sides are clear.

• We’ve got a GTM engine that’s kicking butt

• But there’s so much sh*t to improve upon.

And we’ve done all this in one of the most crowded categories imaginable: fintech + advice.

The leap now is to get to $5M+ ARR and earn the right to declare “product-market fit.” Which is the most bullsh*t generic jargon for "people like our sh*t…and we know it.”

But here’s the kicker: VCs don’t care about vanity metrics. They don’t care that one of my videos hit 4M views last week (which did happen btw…). They don’t care that we closed another enterprise trial. They don’t even really care that our ARR doubled.

They care about one thing: whether this team can adapt and win in a bloodbath category.

In a crowded space, conviction matters more than optimism.

What These Pitches Are Actually Like

In the past month, I’ve met with ~15 funds. Some in person. Some over Zoom. One literally while I was in a park. A few over drinks.

And here’s what I’ve learned: the first five minutes decide everything.

If they’re in, you’ll feel it immediately. If they’re out, nothing you say after matters. And often, they’re looking for an aha moment. No different than the aha moment every founder looks for in their users.

That’s why I skip the small talk. Within the first 15min, they should know our story, have introduced ourselves to one another, and can just jump to the ultimate question:

“What’s your gut reaction? Any burning questions that are top of mind?”

If they’re out, great. If they’re curious, I lean in. I’m not there for approval. I’m there to find alignment and avoid wasting time. No different than them.

And I don’t take it personally. Ninety-five percent of VCs will say no. Not because Habits sucks, but because they’re human. Maybe they’re exhausted. Maybe their baby was up all night. Maybe they’ve seen five pitches that morning and they’re fried. Maybe they got burned by a previous investment similar to us. Maybe they’re more excited about another industry. You get my point….

That’s why I can stack 15 meetings in a couple weeks and not spiral. I read the room, hit the gas if it’s worth it, cruise if it’s not.

Rejection isn’t personal. It’s just signal. The faster you read it, the less it stings.

Closing Thought

Fundraising isn’t some magic unlock. It’s not the key to success. It’s just convincing a few people, at the right time, to bet on you.

That’s why Veera and I treat it as ongoing. We’re always raising. Always testing. Always sharpening. Because you never know what might be around the corner.

Because if you only pitch when you “need” the money, you’ll show up desperate and rusty. And that’s when you lose.

The story matters more than the stage. And the best founders are always telling it.

Feedback for Jack

Enjoyed this newsletter? Forward it to a friend and have them signup. Alternatively, use the referral link at the bottom of this email.

What’s Coming Next?

There’s some big news underway, but I may or may not write about it next week. So stay tuned and have a great rest of your week!

Sharing Is Caring

Do me a favor, if you enjoy this, share it with a friend!