^Introduction

A Day in the Life: Three Founders, Three Realities

The whole reason I began posting online was to demystify the founder journey. When I was starting Habits, all the content out there was from ex-McKinsey consultants, employee #200 at Uber, or some founder who just sold for $100M filming from a penthouse in LA.

Cool stories, but completely unrelatable or just flat out wrong.

So today, we’re pulling back the curtain. Not just on me, but on two other founders…close friends who agreed to share their “day in the life” as long as I keep them anonymous.

Forget morning routines and desk setups. This is about what actually takes up headspace week to week.

^{Top Content From Last Week}

In My Satire Era…

I’ve done some random stuff on social media over the years. Filmed myself doing sales calls, VC pitches, cold calls to users, etc.

But lately, I’ve been playing a character that pokes fun at the problem we’re solving at Habits. You can also watch the video on Instagram if you don’t have TikTok.

@jack_boudreau_

For the record, it’s a walk up in SoHo

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Me (Jack, 30) — $1M Raised, Marketplace

We’re a lean team of ~5–6 people, about to cross $1M in ARR, just opened an office in NYC, reach millions of people per week through content, and our most well known product is the marketplace at www.usehabits.com.

The best way to describe my day to day is constantly thinking about these questions…

• How do we drive more families looking for a financial advisor to us?

• How do we make the experience better, stickier, and simpler?

• Who are the right partners to amplify our reach?

• How do we find amazing employees, AND create an amazing culture?

That’s the loop running in my head 24/7. So my days are a mix of:

• Posting on LinkedIn, TikTok, Instagram, Reddit, writing this blog, etc.

• Cold-calling users & customer service calls with advisors

• Reaching out into the ether for investors, partners, employees, you name it.

At the end of the day, my job is to sell. Sell the vision, sell the product, sell the opportunity.

For example, I’m laser-focused on launching our new partnership vertical. Why? 90% of our users refer. But we also get referrals from CPAs, attorneys, financial education platforms, even employers. In my eyes, amplifying these relationships are our next source of growth.

I’m just trying to maximize our chances of getting lucky…a viral post, an enterprise partnership, a company introducing Habits as the go-to place to find an advisor.

“Jane” (33) — Raised $7M, Enterprise SaaS

Jane has been through YC, sold a company (netted about $500k), and raised $5M out of the gate for her new SaaS startup. They’re at 10 full-time employees, burning through serious cash each month.

Her world is enterprise trials. Three big ones right now. If they convert, each is worth millions a year. But until then, it’s all about “figuring it out.”

Her routine?

• Wakes up at 7 a.m.

• Protects her first two hours for exercise, breakfast, and a slow morning.

• By 3 p.m., she’s basically done. Then repeats, seven days a week.

Her mindset is ruthless: spend the $5M in 24 months. If a trial converts, she already knows which VCs will hand her $10M to scale it. But as Jane describes it, she is just constantly thinking about “should we pivot to something obvious, simpler, or adjacent?”

In other words, Jane and I always joke…I’m a trench warfare kinda guy and she’s the sniper from a mile away.

“Mark” (33) — Marketplace Exit ($6M exit)

Mark sold his marketplace two years ago and walked away with ~$4M after tax. He spent two years with the acquirer, making $200k a year just to “smile and play corporate,” while focusing on family. Two kids, a third on the way.

Now he’s back in founder mode, working on something new (still stealth). His take on “day in the life” is different:

Until you’re at $5M ARR or at least five years in, you don’t “know shit about fuck.” His words, not mine. You’re just showing up every day, doing your best, and riding out the swings:

• Weeks glued to Zoom.

• Weeks traveling nonstop.

• Weeks with zero meetings to “focus.”

He doesn’t measure the business by users, product, or investors anymore. He looks at efficiency. Usage. Marketing reach. Deals. People.

Every day it’s dashboard checks, Stripe refreshes, asking questions. And when growth stalls? You force it…a new enterprise engagement, an acquisition, a capital raise.

And selling? “Selling a company fucking blows.” Nine months of posturing, nine more months of brutal diligence that burns millions in legal fees.

His analogy: entrepreneurship “day in the life” isn’t a marathon or a sprint. It’s a race where you’re told “run to the finish line” but nobody tells you how far, what the terrain is, or when it ends. Some days people pass you. Some days you pass them. Every day is a battle with the race and yourself.

Closing

Three founders. Three stages. Three realities.

One of us is pre-seed, trying to maximize our chance of explosive growth. One of us is scaling through precision. One of us already cashed out with $4M, only to realize the game never really ends.

Different paths. Different routines. Same truth: day in the life is always different’ But the unversal truths are selling, stressing, surviving, and occasionally catching lucky breaks.

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What’s Coming Next?

I’m overdue for a rant about the state of personal finance. I’ve heard and seen some dumb a$$ sh*t online in the last few weeks and feel compelled to share my 2cents.

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