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Introduction:
New Series…
I’m cracking open my calendar and taking you along for the ride. Think of it as “Day in the Life: Jack Edition”—where I juggle travel, investor updates, and an ever-growing to-do list while trying not to lose my mind.
This week alone, I’m bouncing between NYC, BOS, and HOU (because apparently, I hate staying in one place), then diving straight into a Friday packed with back-to-back meetings. And since it’s end-of-quarter madness, I’ll be sharing what’s running through my head—what I’m thinking, struggling with, and what I can say publicly without my co-founder having a heart attack.
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Main Story:
A Look Inside My Calendar
Screenshot of my calendar this week
Sunday:
Flew in from Texas, got settled near MSG (central, easy to get around).
Met up with a college buddy for drinks + football in Gramercy.
Monday:
Early morning routine, then took a train to Long Island for a sales pitch.
Back to Manhattan for meetings with founders + potential partners.
Drinks with a competitor—yes, you can be friendly, just don’t be weird.
Chick-fil-A + Netflix, lights out.
Tuesday:
Met with a potential brand partner for social reach.
Downtown for a check-in with a VC we know well (not raising, just keeping relationships warm).
Lunch with Veera (co-founder convos = startup marriage: we yell, we laugh, we figure it out).
North to meet a founder in our space; Veera met with a new hire starting next month.
Downtown again—big sales pitch through a well-connected friend + got legal insights from his SEC experience.
Stopped by Cuts store for a hat (obviously).
Midtown podcast appearance.
Zoom sales pitch because I couldn’t make it in person.
Met up with an influencer buddy I’ve Zoom’d with a bunch.
Wednesday (as I write this):
A few AM meetings, then hopped on a train to Boston for sales + customer meetings.
Dinner with a former intern.
Thursday:
Travel day back to Houston. Long shower. Healthy dinner. Maximum relaxation. If you text me Thursday evening I’ll likely respond on Sunday LOL.
Friday:
Seven Zoom calls. And then my perfectionist and anxious insecurities will force me to catch up over the weekend.
That’s the game plan. No wasted time, just keeping things moving. Made a Reel (also on TikTok) for you visual learners.
Instagram post by @jack_boudreau_
What’s On My Mind This Week
There are the usual things I track daily—product progress (Veera’s domain), new sales demos, consumer sign-ups, onboarding rates, and all the standard marketplace metrics. But beyond that, here’s what’s really running through my head:
💰 Travel & Spending
I hate spending money. Flights were covered with points. Hotels? Courtyard Marriott with some old JPM codes I found on Reddit—$1,200 for three nights, $250 for Boston, $250 for Amtrak (seriously, screw you, Amtrak).
Probably dropped ~$250 personally on food and another $250 on the company, but most of the time, someone else picks up the tab (which is chef’s kiss).
Even though we have hundreds of thousands in the bank, I was raised to question every dollar. If it doesn’t lead to revenue, why am I spending it?
That said, these meetings? Potentially worth millions. So yeah, worth the spend.
📈 Sales & Product Anxiety
March sales were solid, April renewals are coming, but I always feel like we could be doing more. It’ll be interesting how things change as we continue to pursue larger, more enterprise level opportunities where we sell 10-50 subscriptions at a time.
Ever since we shifted to a product-led experience, I’ve been obsessing over middle-of-funnel drop-offs—people who download the app, make a profile, then ghost.
Got some sharp advice from that competitor I met up with, and now we’re tweaking messaging + website flow to fix it.
Could we pay an expert? Sure. But I believe in paying with time before paying with money—until the balance flips.
🏢 First Big Enterprise Deal
We’ve got 3-4 major companies interested, but each wants something slightly different.
Reality check: We’re a team of six. We can’t take on multiple massive clients at once, so we have to pick the one that will level us up the most.
🚀 End-of-Quarter Momentum
End of the quarter is arbitrary, but I care because I need to write a killer investor update.
People don’t want to hop on a sinking ship—they want to join a rocket.
I’m transparent about numbers and challenges, but with 50+ potential new investors reading these updates, I make damn sure they see the real momentum, not just noise.
That’s where my head’s at. Now, time to execute.
What’s Coming Next?
A lot of you have asked for more versions of the “day in the life” type content. This time I’m going to try my best to document and share everything I’m doing next week, which also includes travel to NYC and Boston. Stay tuned!
Sharing Is Caring
Do me a favor, if you enjoy this, share it with a friend!
