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LinkedIn Grind

My LinkedIn has gotten a lot of love these past few posts, but it’s not surprising. I once heard this crazy stat that nearly 60% of weekly active users earn over $100k.

And since then, it’s oddly become one of my favorite channels.

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The Fallacy of Fundraising

I'm sure like many of you, you see headlines of massive capital raises and think to yourself: “Wow, that company must be crushing it.” But here’s the truth…fundraising is a fallacy.

Don’t get me wrong. It’s hard. It's grueling. It's a full-time job and a half. But the moment you realize that those TechCrunch headlines are no different than your friend’s highlight reel on Instagram, everything changes. Because just like a photo dump from someone's trip to Santorini, that funding announcement only tells 10% of the story.

The Seed Stage Wake-Up Call

I vividly remember my first interaction with a VC-backed founder. This was back in 2021. I was about a year into my associate role on the FIG team in JPM’s private bank. Generally, my job was all about business development. And the venture scene in Chicago was buzzing.

There weren’t many at the bank who really gave a sh*t about early-stage startups, so I just went to town. Every morning, I'd get to the office by 6am, I’d hop on the Bloomberg terminal or into Pitchbook and just spam outreach. Didn’t matter if a company had raised $1M or $100M…I’d reach out. Coffee, lunch, dinner, drinks. I didn’t care. I wanted to meet them.

One company in particular stood out. They’d just raised a $8M seed round. The founders were in Chicago. I had a personal connection to one of the exec’s there, so it felt like my first real opportunity. So I gave him a call, we shot the sh*t, and he intro’d me to the founder. We had a couple good convos, and that’s when it hit me:

Raising money doesn’t mean jack unless it actually builds something valuable.

This founder had a small family, was sharp, doing all the right things, and yeah on paper they had a few million in the bank. But as the drinks started flowing one evening, he let something slip. If the company didn’t hit $20M in revenue or get acquired for $100M+, he’d walk away with about $500k. The FOUNDER.

I was floored. Obviously, I just nodded along, but internally I was screaming: WTF?

Raising money doesn’t mean you’re winning. Sometimes, it means you’ve just signed up to lose slower.

The Founder Gets Pushed Out

A couple years later, that same company raised a $20M Series B. The bank lit up. People were reaching out left and right. Investment banking buddies were texting me for intros like he was the next unicorn whisperer. And six months later… he was “moved” into a Chairman role.

Everyone was like: “Dude! That’s amazing! Huge win!” But here’s the truth: he was pushed out.

Their executive bylaws had a clause “standing CEOs needed at least 5% equity to remain in the role.” On a fully diluted basis, his equity dipped below that threshold, and boom the board had the power to install a new CEO. They weren’t giving him more incentives unless he stepped aside. That’s it. Game over.

And you hear that and go… holy sh*t. That’s common. Way more common than people think. Because most of the best stories? You don’t hear about them. Not because something shady went down, but because they’re nuanced. Messy. Human.

Sometimes the team dynamics change. Sometimes the deal gets so complex that even the founders don’t fully understand who owns what until it’s too late. Sometimes people walk away with life-changing outcomes, and sometimes they don’t—and it’s not always a reflection of the effort they put in.

That’s where the phrase “it’s business, not personal” really starts to show up. Because when you’re raising capital, you're not just picking up checks, you’re setting the terms for what happens if and when things go sideways. And if you’re not thoughtful, things can spiral fast.

Most founders don’t get screwed by the market. They get quietly squeezed out by the terms they didn’t fully think through.

Raising the Right Way

When we raised our $1M round for Habits last year, we kept it tight. Just three funds made up about 80% of the round. The rest came from early adopters and angels who not only believed in Veera and me, but had serious capital and experience to offer.

But friendly reminder: that money? It’s not charity.

I remember a vivid moment. There was this old banking exec who I just continued to pitch and pitch and pitch. And bear in mind, this was only for $15k. It became something I obsessed about. I’d find myself making all these decks, rehearsing pitches and tweaking our messaging every damn day. And guess what? He never invested. And looking back, he never was going to.

So one day, not sure when, I just all of a sudden stop caring. And exclusively focused on our users. Which is of course the moment when everything began to click.

So, yeah, I post a lot about pitching VCs. Mainly because people find it entertaining and it’s a clever way to evangelize our mission. But it’s not the game. It’s not the mission. And most of the time, it’s a distraction.

The work is the mission. Talking to users. Building shit. Shipping stuff. Taking care of our team.

Fundraising should feel like rocket fuel, not a leash. If it feels like a leash, you’re not doing it on your terms.

Always Be Closing (Or Not)

When I joined Techstars after JPM, I told people it was this elite VC gig. In reality, it was a 3-month contract being an associate for an accelerator. But I learned more in those three months than I did in any other role.

Founders would pitch 50+ investors in a week. It was chaos. And I watched some of the best sellers I’ve ever met operate—raising money, making intros, brokering deals. One Techstars MD looked me dead in the eyes and said:

“Jack, you’re always raising. Either closing a round or preparing to open one.”

At first, I hated that. But now I get it. Because the truth is…there’s no perfect deal, perfect round, or perfect moment. There’s just time. And the longer you stick around, the more your timing aligns with the right investor.

That's why we update our investors and interested funds monthly. It's not performative, it's planting seeds. Because this week, we're starting diligence with three funds we’ve known for years. They've watched us build, execute, and become exactly what we told them we’d become.

Will they invest? Maybe. Maybe not.

Long-term trust is built in the quiet months, not the closing ones.

Last story → The Dickhead Associate

And yet... there are still days where I want to rip my hair out.

Just last week, I had a VC associate reach out. Someone I didn’t know. Apparently their predecessor met me a year ago and handed off my info. Fine. Happens all the time. But this guy? Full-blown asshole.

And listen, I have thick skin. I’ve been chewed out in analyst programs, grilled in founder meetings, roasted on social media, you name it. But this dude just had something to prove. He asked a bunch of irrelevant shit, flexed fake knowledge, and acted like he knew more about building a company than I did. Spoiler alert: he didn’t.

And the worst part? He legit wouldn’t shut up about AI and the All-In podcast, plus his experience in [Insert Management Consulting Job]. There are so many gatekeepers in this world, people who’ve never operated, never shipped product, never worked at a startup who are grilling founders for answers they don’t understand the context for.

Not everyone in venture deserves your time. Pick your battles. Protect your peace.

So What’s My Philosophy?

My philosophy on fundraising is pretty simple:

Raise money if it makes your mission stronger. Not your ego. But by no means judge a company or their success based on their ability to raise. Choose investors the same way you choose co-founders, with trust, long-term alignment, and real conversations. And remember that your job isn’t to impress a fund. It’s to build a company that matters.

The best money isn’t just capital. It’s community. It’s partnership. It’s patience.
And it’s the belief that when things go sideways (and they will), your investors won’t just send a Zoom link, they’ll roll up their sleeves and help.

Because this whole thing we’re building? It’s not about the raise.

It’s about what we do with it.

You’re not in the business of raising capital. You’re in the business of building something that outlives you.

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What’s Coming Next?

I got triggered this week, which prompted this edition. But I’ll follow my original plan and next week I’ll dive into how I approach fundraising, building a data room, how I source funds, angel investors, and carve the emails to make it all happen.

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