A few years ago, my idea of a perfect day involved coffee, a workout, and some kind of business breakthrough. Maybe mapping out a new revenue stream. Maybe a long walk while listening to a podcast about why I need five LLCs and a Wyoming holding company.

Back then, I was sprinting. Eyes locked on the prize, whatever that happened to be that week. Time felt infinite. The hustle was the reward. I believed deeply in compounding effort and outworking everyone in the room.

Then I had kids.

And now? Now I believe deeply in getting everyone to nap on schedule.

I still have ambition. Arguably more than ever. But I’ve had to redefine what success looks like and feels like. Before kids, success felt like momentum. Like motion. Like doing.

Now, success feels more like presence. Like being able to pause a call, change a diaper, and get back to work without burning the business down. It’s slower. But strangely, it’s deeper.

I used to think interruptions were the enemy of progress. Now I think they’re the test. Can I get knocked out of flow and still show up? Can I build something meaningful while also molding a human being?

Turns out, yes. But not without tradeoffs.

Tradeoff #1: Time is No Longer Yours Alone

Before fatherhood, I used to fill my time like a Tetris board. If I had 30 minutes free, I’d wedge in a podcast, do some modelling, or a little spreadsheet cleanup. Now? If I get 30 minutes free, well, I’m suspicious!

You don’t realize how much time you waste until you no longer have any.

And honestly, that’s been an advantage. I’ve cut a lot of nonsense from my day. I don’t over-engineer systems anymore just to feel productive. I say no to more projects. Not because I’m less driven, but because I finally understand the cost.

Tradeoff #2: Risk Gets Reframed

I used to romanticize risk. “I’ll just bet on myself,” I’d say. And I still do, but now I’m aware of who else is riding shotgun.

When it was just me, I could front a business idea with my rent money. Now? I have to think about health insurance, college funds, and whether I remembered to order more baby wipes.

That doesn’t mean I’ve lost my edge. It just means I plan better. I look for asymmetric upside. I value cash flow more than headlines. I think more strategically…still adventurous, but with more contingency plans.

Here’s the twist: fatherhood hasn’t dulled my ambition. It’s sharpened it.

Because now, my motivation isn’t just internal. I want to build a life my kids can grow up proud of. I want to be around to see it. That forces clarity.

I’m no longer building a business just to say I built something. I’m building with intention. For flexibility. For legacy. For time freedom. So I can go to the park on a Tuesday without checking Teams every 10 seconds.

And strangely, that clarity has made me more effective. I don’t need to be the busiest guy in the room anymore. I just need to be the one building what matters, to me, and more importantly, to my family.

If you’re in that in-between place, where ambition is alive but your house is covered in Cheerios, just know you’re not alone.

You don’t have to choose between being a present parent and a driven entrepreneur. But you do have to get better at choosing your battles.

Some days, your win will be a client deal. Other days, it’ll be surviving a road trip with toddlers and not enough snacks...Either way, you’re still building. Just with more than spreadsheets now.

And if you’re anything like me, you’ll find that once you stop sprinting, you start compounding in more meaningful ways.

Let me know, how do you balance family and ambition? Or are you still figuring it out like I am?

Drop a comment, reply to this email, or just take a deep breath and enjoy the silence (if you’re lucky enough to find any).

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There are seasons in my life where I try to take on everything.

It usually hits me out of nowhere, this intense need to overhaul my life all at once. I’ll decide I want to start working out again, learn piano, build a business, get serious about writing, become the best dad in the world, read more, eat clean, meditate daily, maybe even learn a new language, because why not? We’ve only got one life, right?

Before I know it, I’ve bought new equipment, signed up for memberships, subscribed to online courses, downloaded twelve apps, and built out some dashboards. It feels like momentum. But if I’m being honest, it’s usually more like panic in disguise.

This never starts from a place of calm. It usually happens when I feel stuck, like I’m treading water in both my personal and professional life. That sense of stagnation builds up until it explodes into a frenzy of “solutions” that all involve me doing more. And fast.

But here’s the problem: doing more isn’t the same as doing better.

I start strong. For a few days (sometimes even a week), I’m energized. Waking up early. Checking boxes. Feeling like I’m finally “maximizing my potential.” But it never lasts. Eventually, one of the new habits slips. Then another. And suddenly the whole thing unravels. I don’t just lose momentum, I get discouraged.

And to make matters worse, I’ve spent a bunch of money along the way. Equipment that gathers dust. Subscriptions I forget to cancel. A reminder that the whole cycle wasn’t just emotionally draining, it was financially wasteful too.

So if you’re someone who also gets caught in this trap of trying to optimize everything at once, here’s something I’ve been trying instead. It’s not flashy. It doesn’t give you that same “new life incoming” dopamine hit. But it works.

The “Too Much” Detox Plan

1. List it all out
Write down everything you’ve been thinking about taking on. Big or small. Fitness goals, business ideas, hobbies, habits, routines. Don’t hold back, get it all out of your head and onto paper (or a Notes app or whiteboard, if you're like me).

There’s something about seeing it all laid out that makes it easier to spot what’s unrealistic.

2. Pick your top 5
This is the hard part. You have to choose. What are the five most important things you want to do right now? This doesn’t mean you’re giving up on everything else forever, just that you’re choosing focus for now.

And don’t forget to include things you’re already doing that you want to keep doing. If you’ve got a workout routine, or you’re spending time with your kids in the evenings, or building something on the side, those count. They take time and energy, and they should be factored in just like any new habit.

3. Fit it into your real life
Once you have your top 5, figure out:

• When you’ll do each one

• Where it fits in your day or week

• How long it realistically takes

Try to build a routine around your life, not on top of it. The goal is sustainability, not burnout.

If you can’t find the time without sacrificing sleep or peace of mind, that’s a signal. You either need to scale something back or delay starting until your schedule opens up. It’s better to move slowly and stick with it than to sprint for a week and burn out.

I’m not perfect at this. I still get swept up in the “do more” trap. I still feel that pressure, the one that whispers you’re behind or you’re wasting time. But I’m learning that chasing ten things at once is often just a distraction from doing the one or two things that really matter.

Sometimes, ambition masks impatience.

Sometimes, busyness disguises fear.

And sometimes, the best thing you can do is less, but with more intention.

So if you’re in one of those frantic phases right now, if your Amazon cart is full of self-improvement gear, or you’re signing up for three new platforms hoping one of them will change your life, take a breath.

You don’t need to do everything.

You just need to do a few things well. Repeatedly. With care.

And the rest? It can wait.

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Last week, I wrote about how easy it is to get stuck in the idea phase, that cozy space where everything still feels like it could be your ticket to freedom. You’re sketching logos, mapping funnels, imagining quitting your job in a blaze of glory. You’re “working on it”, but quietly dodging any real risk.

So this week, let’s talk about what’s usually lurking just beneath that cozy idea purgatory:
the fear of failure.

This is a fear that hits entrepreneurs differently.
It’s not just a fear of losing money, it’s a fear of what that failure means about you.
You had a big dream, talked about it, maybe even built an audience around it…and now you’re terrified that if it doesn’t work, you’ll be exposed. That you’ll have to go back to your day job with your tail between your legs while people whisper, “Guess it didn’t work out, huh?”

I’ll go first.

I’ve definitely been there. I’ve been the guy who didn’t launch, the guy paralyze by fear, more times than I’d like to admit.

It’s not that I lack ideas. Far from it.
I’m usually three steps ahead of myself before I’ve taken step one. Before I have my first customer, I am planning my exit strategy.
The vision is there, how it scales, how it frees up my time, and how I’ll grow the team. But when it comes time to actually hit “publish” or ask for the sale, I start thinking:

“What if this doesn’t work? What if no one buys? What if I tell everyone I’m doing this, and it flops?”

That’s the real fear: not just that it’ll fail, but that it’ll fail publicly.
Because in 2025, your business isn’t just between you and your bank account.
Your family knows. Your friends know. Social media knows.
And if you’ve been posting about “building something,” you feel like you’ve got an invisible audience waiting to see if you make it or fizzle out. Often times, it seems like they are rooting against you.

And then there’s the emotional weight of not being able to fully step into the business.
For me, the dream has always been to pivot fully, to take one of these businesses I’m working on and make it my only thing. So failure wouldn’t just mean a project didn’t work. It would mean being stuck in the in-between: still needing a job to support the thing I wish could support me.

It’s frustrating. Paralyzing, even.
And it’s easy to mistake this paralysis for “being strategic” or “waiting for the right time.”
But if I’m honest? It’s fear, plain and simple.

What I see in others

When I talk to other entrepreneurs, or people who want to be, the fear is often the same.
They’re afraid of the financial risk. They worry about debt, about sunk costs, about disappointing their family or having to explain to their spouse why their life savings just bought them 200 custom t-shirts and a Shopify store with no traffic.

A lot of people put everything on the line, and if it doesn’t work, they feel like they’ve lost their identity. Like they failed not just at business, but at life.

And the worst part? Most of them keep going, not because they still believe in the business, but because they feel like they have to.
They’re stuck.
It’s the sunk cost trap.
They’ve borrowed money, made public declarations, sacrificed sleep, and now the thought of pulling the plug feels like admitting defeat, so they keep pouring in more time, more energy, more cash.

It’s painful. But it happens more often than you think.

So what do you do?

Here’s the perspective I’m trying to adopt, and maybe it’ll help you too:

You don’t have to win to grow.

You just have to try.

If you give something your all, your best work, your full attention, your strategic brain, and it still doesn’t work? That’s not failure. That’s real-world experience. That’s the kind of MBA you won’t get in the classroom.

You’ll learn things that will take years to learn at a 9-5.
You’ll develop instincts, resilience, resourcefulness.
You’ll understand your limits and your potential better than ever before.
And all of that will serve you, in the next business, the next pitch, the next version of yourself.

No one wants to fail. But I truly believe that controlled failure, the kind where you’ve done the prep, taken calculated risks, and protected your downside, is not only survivable… it’s essential.

I’m not saying bet your house on your startup.
I’m saying: build the plan, run the numbers, talk to people who’ve done it, and take the shot.
Make sure your risk doesn’t ruin you and take it.

Because playing it too safe?
That’s a quiet kind of failure that takes longer to notice, and hits harder when it finally shows up.

Let’s Talk

Are you building something and feeling the fear?
Have you already built something that didn’t work out?

If you’ve tried and failed, I want to hear from you.
I’m writing a book about lessons from failed businesses, and I’m looking to talk with people who have stories to share, the messy, painful, insightful kind that can help others do better.

I genuinely believe the greatest lessons come from failure, and sharing those lessons is far more valuable than the typical “here’s how I succeeded” story.

If that’s you (or someone you know), reply to this email or shoot me a DM.
You can stay anonymous, or you can comment below…your call!

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After Broposals, even though we weren’t successful in turning it into a profitable venture, it lit a fire in me.

I was excited.

Every day felt like a new opportunity. A new problem I wanted to fix. A business idea waiting to happen. I got hooked on that feeling. That adrenaline rush of starting something. It was like a drug.

And that… was the problem.

I was so obsessed with chasing that high, the excitement of the idea stage, that I never slowed down long enough to build anything real. I’d get a spark of inspiration, pitch it to my wife or my friends, and feel the dopamine hit when they said, “That’s actually a great idea.”

But that’s all they ever were.

Thoughts.
Ideas.

They never made it past the whiteboard or voice memo.

The first time I remember feeling that rush was when we got our first client, my personal trainer, Mike.

We had just wrapped up a discovery call to talk through what he envisioned for a fitness-themed gift box for his groomsmen, and afterward, we hit the ground running. We stayed up until two or three in the morning mapping out all the things we thought could work and why. Protein samples, customized shaker bottles and gym towels, motivational wristbands…we were on a roll.

That brainstorm snowballed into other themed boxes we could create. Outdoors. Military. Gamer. James Bond.

And instead of focusing on fulfilling that first box (for our first actual client) we drifted into planning five themed sets.

We mistook motion for action.

Looking back, that moment wasn’t unique. It was the start of a pattern.

I can’t even count how many “next big ideas” I have run through over the years.

Each one started with that same spark. The excitement. The flood of possibilities. I’d start mapping things out in my head. Sometimes I’d throw together a name and logo. Sometimes I’d buy the domain. Sometimes I’d even start a pitch deck or basic landing page.

But the moment things got difficult, the moment the buzz wore off, I’d quietly move on.

I was planting seeds, then walking away before anything could take root.

One thing I’ve always been drawn to is the numbers. I love building out financial models.

Forecasting revenue.

Calculating breakeven points

Playing with scenarios.

That part came easy to me. It made me feel productive. In control.

What was harder?

The rest of the plan. Actually defining the target customer. Summarizing market research. Writing down a real marketing strategy. Creating a go-to-market roadmap.

I’d spend hours building an awesome looking, fully dynamic financial model, loaded with startup costs and unit economics and tabs for scenario analysis. And then I’d stare at a blank page where the operational plan should be, unsure of how to turn the vision in my head into something real.

Once I hit that wall, the excitement would fade.

And the idea? It would quietly join the archive.

I was more in love with the idea of being an entrepreneur than the actual work of it. I pictured the success, the freedom, the recognition, but not the grind it takes to get there.

Because here’s the reality behind the dream:

• 25% of businesses fail in their first year

• 50% by year five

• 65% by year ten

• And the average income for a small business owner?
  $20,000 in year one. $65,000 in year five.

And that’s if you make it to year five.

You add in the 80-hour weeks, missed weekends, skipped holidays, family time sacrificed… and suddenly that steady paycheck with PTO starts looking pretty good.

Even with that, something in me keeps coming back to this idea of building something on my own. Something real. And I’ve had to confront the reason I never followed through before.

One reason?

Validation without risk.

If I could share an idea with people I trust and get a little buzz of encouragement, then I didn’t have to put myself out there where failure was real.

As long as the idea stayed in my head, it was perfect. Untouched. Potentially brilliant.
The moment I tried to build it, I risked proving it wasn’t.

But I’ve learned something the hard way:

If you only chase the feeling, you’ll never create something real.

Ideas are easy. Execution is everything.

And no matter what you're building, a business, a new career, a healthier lifestyle, you will hit the dip. That moment where the fun wears off and you're left with nothing but friction.

That’s where the work starts.

Not at the peak of the high. Not when everyone’s excited. But in the quiet, unglamorous middle, when no one’s watching and everything feels hard.

If you can stick through that, really grind it out, that’s where the next version of you is built.

And yet, even when you know that, there’s another force at play that can stop you dead in your tracks:
fear of failure.

That’s what I’ll be writing about next week, the fear of putting yourself out there and it not working.
Where it comes from.
Why it’s so powerful.
And how I’ve let it hold me back more than I’d like to admit.

If this post resonated with you — if you’ve ever found yourself chasing the feeling but never getting to the finish line — I’d love to hear from you.

Leave a comment, reply to this email, or share the post with someone else who might relate.
Let’s build, break, and rebuild together.

See you next week.

I’ve always had ideas. Some big, some kind of ridiculous. But my first real attempt at building a business, something my brother and I actually tried to get off the ground, never really went anywhere.

Not because the idea was bad. In fact, I still think it has potential.

It just died under the weight of inexperience, bad timing, and the brutal reality of what it actually takes to make a business work.

The Idea: Broposals

Back in 2016, I was a broke college student, recently engaged, and wanted to do something special for my guys to ask them to be in the wedding party.

We had seen some creative ideas floating around online, so my fiancée and I got to work. It took a ton of time and effort to get everything together, but in the end, it came out great. Our friends loved it.

My older brother Parker, one of my groomsmen, looked at everything we had pulled off and said, “That seems like a lot of work. This should be a business.”

My wife, who is infinitely more clever than me, immediately shot back, “You should call it Broposals.”

And that was it. The wheels started turning.

We mocked up some early concepts, talked about product lines, and even landed our first customer: my personal trainer Mike. He was recently engaged, heard about the idea during a workout, and was hooked. He wanted something with a fitness theme, so we got to work.

We built a custom set for his groomsmen. He gave feedback. We made six more. He loved the final product.

Momentum was building. Kind of.

What Went Wrong

Looking back, it’s easy to see why Broposals never really got off the ground. There were two big problems and a dozen smaller ones.

First: money.
I was still in school. My bank account was floating in the decimals. We had big ideas for creating themed groomsmen gift sets, not just shot glasses and flasks thrown into a box, but fully customized collections based on each groom’s personality or hobbies.

One client got a fitness-themed set with a monogrammed gym towel, protein sample packs, and a personalized shaker bottle. Another was into hiking and got a rugged outdoors set with a multitool, a firestarter, and a stainless steel flask engraved with “Take a hike (but in a suit).”

We wanted every set to feel intentional. Curated. Like it came from someone who actually cared.

But to offer real customization at a price point people could afford, we would have to buy a lot of inventory in bulk. And we just couldn’t.

Second: product quality.
Everything affordable online was absolute garbage. Broken flasks, scratched-up glassware, knives that wouldn’t close properly. The higher-quality stuff pushed us into a price point that didn’t make sense for our target market. And sourcing was a nightmare.

Then came packaging, which turned into our biggest logistical headache.
We needed each set to be secure enough to ship, but also nice enough to feel like a gift. We explored custom foam padding and box inserts, but they were expensive and inflexible. And again, they required bulk orders we couldn’t afford.

We were stuck.

What We Didn’t Even Get To

We never made it to the more complex parts of launching a real business.
We didn’t touch marketing or customer acquisition.
We didn’t build out inventory management or fulfillment processes.
We didn’t launch a website or figure out how to take payments.
We never dealt with legal, tax, or compliance.
We had no plan for returns, customer support, or storage.

We were just two broke guys with a clever name and a cool idea, trying to duct tape it into existence.

It was one of the most exciting and frustrating times in my life. I still think that if I had just been a little further along — out of school, with a job and some savings — we might have pulled it off. Or at least taken a better swing.

Sometimes I wonder what Broposals could have become. Around that time, Man Crates was blowing up. That market was real. Maybe we could have tapped into it.

And yeah, the name was awesome 😎

What It Taught Me

That early failure didn’t feel like a crash. It felt like a slow fade. But it stuck with me.

I learned that product-based businesses are hard. Really hard.
I learned that having an idea is nothing without execution.
I learned that creativity and hustle might get you started, but they won't get you to the finish line without systems, capital, and structure.

Most of all, I learned that starting is easy. Building something real takes more.

What’s Next

That first attempt gave me a glimpse of what building something could look like, even if I didn’t get far.

Next week, I want to talk about the trap I kept falling into after Broposals; the addiction to ideas. Always thinking, always planning, but rarely following through.

If you've ever found yourself stuck in that cycle, next week’s post is for you.

Thanks for reading. And if you’ve got a dusty idea like Broposals buried in your past, I’d love to hear about it. We all start somewhere!

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I’ve spent a lot of time feeling like I wasn’t moving fast enough.

Like I should’ve built more by now.

Like I should have it more figured out.

But here’s the truth:

I’ve started three businesses so far.

• One burned out.

• One I built successfully and sold.

• And one, my current venture, is growing steadily.

This blog isn’t about overnight success or building a unicorn.

It’s about documenting the real stuff. The experiments, systems, failures, and small wins (in business and in life) that stack up over time.

1. Why this, why now

This year, I made it a point to start reading more, both for inspiration and direction.

One common theme that keeps coming up is this:

You don’t need the perfect setup to get started.

When you begin something, anything, it will grow, evolve, and improve over time.

If you wait until everything is perfect or the timing feels just right, you might end up waiting a lifetime.

I also believe writing out my processes will help me stay consistent with the goals I’m setting, both personally and professionally.

It’s a form of accountability, but it also gives me clarity. Putting things into words helps me see what’s working, what’s not, and what I might try next.

That’s exactly what I’m doing here.

2. What you can expect

This isn’t a polished masterclass on entrepreneurship.

It’s a working journal, written in real-time, about what I’m building and breaking.

Expect things like:

• Marketing tests that flop (and a few that work)

• Behind-the-scenes breakdowns: pricing, hiring, growth

• Lessons from selling a business

• Business model deep-dives

• New ventures I’m testing

• And probably a few honest rants when things go sideways

I’ll keep it honest, useful, and hopefully entertaining - even if it’s messy.

3. Who this is for

If you’re:

• Building a small business

• Thinking about starting your first one

• Trying to get unstuck

• Or just curious what it actually looks like behind the curtain…

This blog is for you.

4. Why “Build // Break // Repeat”?

Because that’s what this journey actually looks like.

You build.

You break.

You learn.

You rebuild, hopefully better than before.

That’s what I’m doing. And I’m inviting you to follow along while I figure it out.

If that sounds like your kind of thing, subscribe and stick around!

P.S. If you know someone who’s building something too, forward this to them.