Jack Boudreau

personal finance // startups // Chicago sports

[Jack Boudreau @jack_boudreau_]

Boy math is looking at a guy with 40+ years of career experience and 10 exits under his belt and thinking to yourself… “dang, I’m falling behind.”

[Jack Boudreau @jack_boudreau_]

@MrBeast I’m in! My username is jack_boudreau_ on Insta and TikTok!

[Atlanta Ventures @AtlantaVentures]

We’re excited to announce our investment in Habits! 🎉

Led by @jack_boudreau_ and @VeeraBudhi, Habits is redefining the way the younger generation connects with financial advisors!

📖 Learn more about why we invested: https://t.co/44vi44OhCC

[Jack Boudreau @jack_boudreau_]

@markcecchini 🐐

[Jack Boudreau @jack_boudreau_]

Millennials are walking a financial tightrope.

You're trying to save for your kids' college funds while also figuring out how to care for your parents as they age. All while attempting to keep your own retirement plans on track.

When I was growing up, money talk was off-limits in our household. It was as if discussing finances was akin to airing dirty laundry in public.

Fast forward to today, and I'm seeing this same money stigma becoming one of the biggest barriers preventing people, especially millennials, from achieving their financial goals.

It's a cruel irony.

We're comfortable oversharing the intimate details of our lives on social media. We openly discuss our fitness goals, career ambitions, and relationship struggles. Yet when it comes to money, we suddenly clam up.

This silence is particularly challenging for the "sandwich generation" – those caught between supporting both their children and aging parents. But you don't have to navigate this alone. In fact, you shouldn't.

Proactive planning and clear communication can help families make difficult life decisions.

Here are a few strategies I've seen work:

1. Break the money taboo: Schedule monthly "Family Finance Fridays" to normalize cash talk.

2. Draw your financial battle lines: Define your support limits before emotions cloud judgment.

3. Secure your own oxygen mask first: Automate retirement savings – Future You will thank you.

4. Educate your kids: Involve them in real financial decisions, not just piggy bank lessons.

5. Hire a financial quarterback: Find an advisor who can help you call the right plays

How do you approach money conversations with your family? What strategies have you found effective for breaking the "money taboo" in your household?

[Jack Boudreau @jack_boudreau_]

The world is obsessed with big numbers.

But as we've grown, I’ve realized that bigger IS NOT always better, especially when it comes to our network of financial advisors.

From day one, my goal was to empower the next generation of families to take control of their financial future.

You might think that having hundreds or thousands of advisors would be ideal. More options, right? Well, not exactly.

We've intentionally kept our advisor network small, under 100. Why? Because we've learned that quality beats quantity nearly every damn time.

It's like going to a restaurant with a menu that has 200 items versus one with 20 carefully crafted dishes. Sure, the first option gives you more choices, but it can also lead to decision paralysis.

When people come through our platform, they're typically presented with three to five advisor options. We've found that this curated approach leads to better outcomes for our users.

We're not interested in providing a "Yellow Pages" experience. That doesn't work well, and it doesn't align with our mission of making financial advice accessible.

Instead, we focus on quality. Every advisor on our platform has been carefully vetted and chosen because they align with our values and understand the unique needs of our millennial and Gen Z users.

This approach allows us to maintain a high standard of service – we can ensure that each advisor is exceptional at serving the specific needs of young families.

It also means we can provide a better experience. With a smaller, more focused network, we can really get to know our advisors and match them more effectively with the right clients.

In your experience, what are the pros and cons of being part of a smaller, more curated network versus a larger, more open platform? What strategies do you use to build trust and establish long-term relationships, especially those who may be new to financial planning?

Let me know!

[Jack Boudreau @jack_boudreau_]

I HATE spreadsheets.

If you’re planning your financial future, they’re a waste of time.

In 2024, you only need one number:

↓

When I started my career, I tracked every penny. I'd spend hours poring over complicated budgets, only to abandon them a few weeks later. It was frustrating and demotivating. But then I stumbled upon a simple concept that changed everything.

Instead of managing a dozen different financial goals, you choose one crucial number to hit each month. This could be your student loan payment, 401(k) contribution, or savings target. The power of this approach lies in its simplicity.

"There's always a new excuse to not hit that number," I often tell people. "Last month it was the holidays, this month it's a vacation. But that's why it's honestly the most integral thing."

By focusing on one number, you cut through the complexity of budgeting and create a clear, achievable goal. This approach works because it's flexible – your "number" can be tailored to your specific financial situation and goals.

For me, that number was maxing out my 401(k) contribution. It seemed impossible at first, especially when I saw my colleagues splurging on fancy watches and designer clothes. But I made a commitment to hit that number every month, no matter what.

What's your number going to be?

[Jack Boudreau @jack_boudreau_]

The key to saving more isn't always about spending less.

No matter how tight money might be, always treat yourself.

The "Special Drink" Strategy

↓

What if I told you that buying a $5 Fiji water could be the key to your financial success?

Sounds crazy, right? But hear me out.

Every single time you go to the grocery store, buy yourself an overpriced drink. It could be a fancy lemonade, an artisanal tea, or yes, even that $5 Fiji water.

Now, you might be thinking, "Jack, have you lost your mind? How is spending more money going to help me save?"

Well, human beings are incentivized creatures. We need something to look forward to, a small reward that keeps us motivated on our financial journey.

By allowing yourself a small indulgence, you're creating a positive feedback loop. You're reinforcing the good habit of grocery shopping (which is generally more economical than eating out) while giving yourself a little treat that won't break the bank.

This strategy works because it acknowledges a fundamental truth about human nature: complete deprivation often leads to burnout and failure. By building in a small, controlled "splurge," you're more likely to stick to your overall financial plan.

Think of it as the financial equivalent of a cheat meal in a diet. It satisfies that craving for luxury or indulgence, making it easier to stay disciplined in other areas of your spending.

What's your "special drink" going to be?

[Jack Boudreau @jack_boudreau_]

A counter-intuitive way to measure success:

“Recurring compliments”

↓

In the early days, it's easy to get caught up in chasing big, flashy milestones:

→ Hockey stick growth
→ Eye-popping DAU
→ Headline-grabbing rounds

But recently, we've been receiving a flood of feedback from our users: "Your service is just so obvious. It's such a need."

When customer after customer tells you that your product fills an obvious need in their lives, you know you're onto something special.

This feedback shows that you've found a real problem, created a solution that works, and consistently deliver what users need.

You might be thinking, "Jack, that's not exactly groundbreaking praise." And you'd be right.

Rome wasn't built in a day.

[Jack Boudreau @jack_boudreau_]

Let's talk about the elephant in the room:

We've all heard it a million times, right? "Start saving for retirement as soon as you land your first job!" But what if that advice is holding us back?

I'm not saying you should blow all your cash on avocado toast and fancy lattes. But I've seen too many people my age living like hermits, obsessing over their 401(k) balance while life passes them by.

Unfortunately, we have no idea what the world will look like in 30, 40, or 50 years. Think about how much has changed just in the last decade. AI, remote work, the gig economy – our parents couldn't have imagined half this stuff.

So why are we still planning our futures based on their playbook?

I've talked to countless retirees, and you know what I hear time and time again? "I wish I had traveled more." "I wish I had taken that risk." "I wish I hadn't waited so long to pursue my passions."

It’s time for a wake-up call.

[Silver Waves Media @SilverWaveMedia]

@adamjcook_ @campus_ink @nil_store @yumbrands @TheRecruitScoop @Cuse_MBB @Cuse @SyracuseU @AndrewPetcash @ProfluenceCap @austingwalton @bgreenwell23 @instagram @Meta @Blake_Lawrence @opendorse @bcope51 @AthletesOrg @brepowerskirk @Intuit @turbotax @cale_johnston @Roy_ReturnOnYou @caseydschwab @AltiusPartners @ChaseQB11 @UCLAFootball @UCLAAthletics @UCLA @christiandawk @SerosPartners @browntown1919 @AthleteNIL @AdvanceNIL @Dan_Furman @502_Circle @DanShellSports @unitedtalent @DanielPoneman @heitner @HEITNERLEGAL @DashSperling @OvertimeElite @DebSpander @InsightSportsLA @DougFillis @Coach_D_Stew123 @BYUMBB @BYUCougars Congratulations to Co-Founder & CEO of Habits, Jack Boudreau, on being named to the 70 Most Impactful People in the NIL Space list.

@jack_boudreau_

https://t.co/v6CdqKh4jr

[Jack Boudreau @jack_boudreau_]

Here's something they don’t teach in college:

You’re in your late 20s or early 30s and staring at a mountain of student debt wondering how you’ll ever buy a house.

Or you and your spouse just had a new baby, and you’re feeling like there’s no way to balance life and career.

Perhaps you're killing it at work but can't shake the feeling that you're on the wrong path and afraid of what’s to come.

There's this gnawing sense that you should have it all figured out by now. After all, isn't that what being an adult is all about?

But this is the biggest lesson I’ve learned over the past decade: most adults are just winging it.

That personal finance class in high school (if you even had one) didn't actually prepare you properly for the real world.

At Habits, we see this all the time. People come to us feeling overwhelmed, confused, and frankly, a little embarrassed.

They've been DIYing their finances for years, cobbling together advice from Reddit, YouTube, and that one friend who seems to have it all together.

But no one can figure this all out on their own. And that’s why I built Habits — to help you get to where you want to be, even if you're not quite sure where that is yet.

College isn’t the end of your journey—it’s the start.

[Jack Boudreau @jack_boudreau_]

My favorite influencer hook is the following.

"Financial advisors rob you, they're schemers & crooks...but if you comment 'growth' I'll share my free investing guide and a promo code to my 18 week course!!!!"

Like seriously...

When are personal finance influencers going to face the same regulation/requirements that licensed professionals have to face.

It makes no sense in my eyes that CFPs, CFAs, and other exceptionally trained professionals have more barriers to share than the influencer who woke up one day and decided to post about crypto.

[Jack Boudreau @jack_boudreau_]

You can’t just jog through life.

At 7AM, I’d show up to Techstars, bleary-eyed & determined, ready to absorb everything the program had to offer. From pitch practice to founder talks to one-on-ones with mentors.

By 10 PM, when most people were heading home, my real work was just beginning. The hours between 10 PM and 2 AM became sacred—it was when I'd apply everything I'd learned that day.

I'd frantically scribble notes during talks, then stay up late implementing new strategies for Habits. Tweaking our onboarding flow at midnight, or revising our pitch deck early in the early hours of the morning.

I pushed myself to the absolute limit day after day. When I was bootstrapping, I was determined to make the most of every single minute.

Was it sustainable long-term? Absolutely not. But sometimes in life, you have to go all-in, even if it means sacrificing sleep and sanity for a small period.

Life is a marathon, but don’t be afraid to sprint.

[Jack Boudreau @jack_boudreau_]

Tell me a story about your craziest workday:

Mine started at 2AM in Vietnam, and I'm on a call with financial advisors back in New York. The hotel room is dimly lit, my laptop screen the only source of light as I discuss market trends from halfway around the world.

My journey building Habits has been filled with moments like these — boarding flights in Nuremberg while explaining our platform to curious families, closing deals in between connections.

Startups often sound glamorous, but the reality is far from it. Building a company is exhausting, disorienting, and at times, lonely. But these experiences gave us something invaluable — an intimate understanding of our customers that no other research could provide.

In the past two years, I've personally spoken to over 1,500 financial advisors and more than 2,000 families. Each conversation, whether at odd hours or in unusual locations, added another piece to the puzzle that’s now known as Habits.

This hands-on approach is now a major competitive advantage. While other fintech startups were relying on algorithms, we built relationships with customers.

Now, our customers feel like a family.

[Jack Boudreau @jack_boudreau_]

It always makes me chuckle when someone tells me they’re pursuing an MBA because they want to be an entrepreneur

[Jack Boudreau @jack_boudreau_]

*Trains for years, arguably decades*

*Grows up being one of the best*

*Earns opportunity to swim at the biggest stage*

*See’s @katieledecky swimming in the opposite direction*

That has to be one of the most humbling experiences of all time

[Jack Boudreau @jack_boudreau_]

I met with a guy last week with a $5M-$10M net worth.

Has never invested in mutual funds, ETFs, you name it.

Want to know whe he invests in?

“Soil” (as he put it)

He’s a farmer/rancher.

Doesn’t invest in things he doesn’t understands.

I loved his opinion because you should always invest in things you understand.

Everyday on social media I stumble upon a new way to cut corners through drop shipping, currency trading arbitrage, purchasing homes with no money down, being my own back, the list goes on…

Those people have a fraction of this farmers net worth.

Why?

Wealth creation takes time, patience, and oftentimes someone who helps or stops you from making foolish mistakes.

It’s one of the many reasons why I am incredibly bullish on financial advisors.

An expert who understands you, your goals, aspirations, acts as a sounding board, business partner, life coach, or anything you need them to be.

[Jack Boudreau @jack_boudreau_]

Raising capital is one of the most thrilling, but also challenging things to do.

I’ve already made the mistakes for you!

[Jack Boudreau @jack_boudreau_]

"I’ve been thinking about getting someone to deal with my stuff since I don’t have time, but I’ve struggled to find an advisor that I think is smart enough to handle my money.

Maybe I’m a bit of an egomaniac, but I feel like 40% of my attention is better than 100% of some of these guys…"

^^^ a direct quote from an email response this AM

I've had the pleasure of meeting and helping investment bankers, institutional traders, private bankers, financial advisors (yes you read that right), private equity principals, VC partners, real estate agents, CPAs, attorneys, and plenty of other... highly skilled and educated.

Oh and by the way, the majority of them have a financial advisor.

Why?

Because they recognize to level up in life and business you have to build a team of professionals who can do the job better than you can.

The tough part is that it's easier said than done.

When I was going through the process to build mine, I was subject to influencers, a few other marketplaces, google search, friends & family, but it was all so chaotic and messy. Plus I just didn't have the time.

That's why we built Habits.