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Help First, Invest Later: Zap’s Playbook for Building Founder Community and Winning Deals

This week, we have a guest post we are excited to share with our readers!

Meet Zap (aka Haley Zapolski), an unconventional investor who started with a $5,000 angel check and has since built a 21-company portfolio by genuinely caring about helping founders win. Without a finance degree or founder background, she's created a unique approach centered on Nashville's startup ecosystem, proving that authentic relationships and doing the actual work can be more incredibly powerful… even without big logos or famous connections. 

Her philosophy is simple: find great founders before anyone else notices, ask what they really need, and earn your place on the cap table by delivering real value first.

My Playbook for Helping Founders Win

I never dreamed of being an investor, I just really liked helping founders win. 

I don’t come from a traditional VC background, no finance degree, or pedigree job. I’m not a former founder. I became obsessed with startups during my first job doing growth for an early stage startup and just…kept going. 

After years of building a founder community through events and education, I started investing. I always took the founder path: start with what you know, figure out the rest as you go.

My first angel check was $5,000. This wasn’t life changing for the startup at all, but it changed everything for me to put my own money on the line. 

When the cap table came back, my name was right there next to the other investors. It didn’t matter that their checks were bigger. I was in the game. That little moment, seeing my name as a shareholder, was addicting. An obsession was born.

Now, I have 21 portfolio companies and just finished doing my 4th SPV. Like the founders I back, I am just getting started. 

People wonder how an outsider like me does it, and the truth is, my playbook is simple. And you’re welcome to steal it! I would love for more people to help startups win in this way. And anyone can do it.

It all starts with the founders

For me, it starts with finding the best founders in Nashville. A lot of people say there aren’t enough great founders here. I don’t buy it. They’re just not looking close enough. 

I make a point of meeting people before they even start their companies, when the idea is still messy and the spark is raw, before it gets polished into a pitch deck. That’s when I want to show up as your first true believer. Before traction. Before headlines. Before hype.

Most of the time, I decide to invest before there’s even a company to point to. What I look for are founders who love to build. The ones signing up for the whole founder journey. The highs, the lows, and most importantly, the unglamorous middle.

I like to invest in nerds and in cowboys. In people who see building as the opportunity of a lifetime. Who couldn’t imagine doing anything else. Who treat it like a craft, a responsibility, a privilege, even a dream come true.

And sometimes? Even good deals don’t fit my framework. I’ve met folks who I know could build successful businesses, but feel like they are only in it for the outcome of getting rich (sometimes they tell you that too). And look, I want to make money doing this too. But the odds are so low that if you don’t also love the ugly parts, it’s going to be miserable. So those founders aren’t a fit for me. I try to send them to other investors. Because for me, building is the most fun thing I could possibly be doing and I want to back founders who feel the same.

When I think about the type of founder I love to work with, I think about Grace Hanson, who’s building Elysian, AI for insurance claims. Now, I never thought I could get excited about insurance claims. But if you’ve ever met Grace, you know what I mean. She carries this energy that makes you believe this is the culmination of her life’s work. Everything she’s done as a five-time chief claims officer feels like it led her to this exact moment. Grace could easily retire and be done. Instead, she’s taking a giant swing at building a billion-dollar business. Because she can’t not do it. That’s founder spirit. That’s what I index for.

This year alone I’ve done SPVs alongside Khosla, Chris Sacca, and Tim Connors. I usually meet founders before the brand names show up. But since I know other people care about signal, there you go (: There are great deals in Nashville, check back in 5 years. 

Asking What They Need

Once I find a founder, the first thing I ask is simple: What do you need help with?

The answers almost always fall into the same three buckets: customers, talent, or capital. Usually in that order. Most investors say they help with these things. But that’s not the problem I’ve found. 

Founders are terrible at asking for help. 

They’re heads down. They think their problem is unique. They have little faith anyone can or will actually help. They feel like they need to project confidence to their investors. And a dozen other excuses. 

Put simply, the best founders are problem solvers, so their blind spot is they don’t even realize what they should be asking for. If you’re waiting for them to come to you, you’re going to miss it. 

That’s why I see it as my job to 1) Ask a zillion questions and listen closely for the cracks between the lines and 2) Take what I hear and go to work on their behalf.

And here’s the kicker, I don’t have a big VC logo behind me, or a Rolodex of billionaires on speed dial. So how can little ol’ me sometimes be more helpful than the “big boys”?

Simple: I actually do the work.

It sounds easy, but it’s not. Getting founders to open up requires time, trust, and showing them you’ll follow through. Once they believe that, the conversations change. They stop with the “we need more intros” fluff and start telling you what’s really hard. That’s when I can jump in.

For example, founders almost never ask to meet other founders to learn from, but sometimes I just see a fit. So I just make it happen. That’s the difference, most VCs wait until a founder begs, then maybe send one email. I try to anticipate the need, connect the dots, and go to bat.

And honestly? It’s not magic. It’s just caring enough to listen deeply and then putting yourself out there. Turns out a well-crafted cold email, a thoughtful intro, or just doing the legwork is ridiculously powerful. And the best part? Literally anyone could do it.

Take Luis, one of my portfolio founders. He was selling to scaling restaurant brands. I didn’t know any restaurant owners. I definitely wasn’t well-connected in the industry. But I knew the problem he was solving and I believed in him. So I emailed restaurateurs until one said yes. That became his first customer. Later, Khosla backed the company and the round got hyper-competitive. But I had already earned my spot on the cap table because I helped before the brand names showed up.

On the talent side, I’ve been lucky enough to help put together eight cofounder teams in the last two years, which blows my mind. Honestly, it’s just by playing the long game, consistently bringing builders together at events, keeping in touch, and always asking myself: Who needs to meet who?

Take Dan and Seth. I had known both of them for a couple of years. Not because they were actively building, but because I make it a point to spend time with former founders and operators even when they’re “between things.” I want to be the first call when the day comes that they’re ready to start again. So when Dan finally decided to build, he called me. And I knew exactly who to introduce him to: Seth, who had been looking at startups to join for over a year. The rest is history because today they’re building Listening Post together!

And finally, the big one, capital. People act like fundraising is this mysterious dark art. It’s not. It’s outbound sales. You just have to care enough to keep selling on behalf of the founders you believe in. I’ve personally sent hundreds of decks, and when I first started I had zero clue what I was doing. Most of my early emails were hope-and-a-prayer energy. But I learned. VCs gave me feedback, coached me, and over time I got better at matchmaking founders with the right investors. To date, I’ve helped raise over $10M for my founders. Not because I have all the answers. Not because I’m the most connected person in the room. But because I’m willing to show up, do the work, and keep going until we win.

Creating Founder Density

People think Silicon Valley is the best place to build a startup because of the money. I don’t. 

I believe it’s the best place because you’re surrounded by founders everywhere you go. Money is geographically fluid. Good deals get funded no matter where they are. But founder density? That’s what changes everything.

In Nashville, I leased 2 old houses next to each other specifically to put my founders next to one another. A place where founders can work, but more importantly, gather. To swap stories. To talk about the things only other founders really understand. To realize you’re not crazy for feeling the way you do. We call it The Lighthouse.

Our belief is simple: one of the biggest drivers of success is being surrounded by other founders at your stage and just ahead of you. That’s where the best help comes from. Not some advisor on a pedestal, but the founder who just lived through the thing you’re going through right now.

Board drama? We’ll introduce you to someone who just survived it (often over a beer).

Lost a cofounder? Talk to someone who rebuilt their team.

Ran out of money? Sit down with founders who clawed their way back.

Lost your biggest customer? Get coached up by the one who turned it around.

Recently, it’s been especially fun to watch Joey Kim pay it forward. Joey spent a decade as a VC before becoming a founder himself, and now he’s crushing it with Longview. Nashville doesn’t have a long history of venture-backed founders, so for many, raising money is uncharted territory. Joey has become that go-to resource for fundraising strategy, narrative building, and running a process. And here’s the best part, he expects nothing in return.

He knows I believed in him at the very beginning. Now he brings that same energy to the founders coming up behind him. That’s the magic of The Lighthouse. 

I don’t pretend to be the expert on building a company. I’m just the triager in the middle, creating space where the founder who “just did the thing” nine months ago can help the one stepping into it today.

One more secret: most founders don’t think they need to talk to other founders.

Most of mine are heads down, allergic to anything that even smells like “networking.” They’d rather grind on product than grab coffee with peers.But here’s the thing- I help them first. Then nudge them into a conversation with another founder. And almost every time, I hear the same thing afterward: “Wow, I had no idea how helpful that was. I didn’t realize there were other people dealing with the exact same stuff I am.”

That moment, when they realize they’re not alone, is priceless.

Help First, Invest Later

Notice, we still haven’t gotten to the investing part. That’s intentional. I think most investors get it backwards: write the check and then try to help. 

I help first. It’s my diligence. It’s how I earn my spot in the most competitive deals. 

Take Jimmy Speyer, founder of Glasshouse. I met him when he was pre-product, pre-revenue. From the start, I knew Jimmy was a winner, so I wrote a small check. But the real work came after.

Over the course of building Glasshouse, I got to introduce him to his first customer, and later his biggest six-figure customer. I helped him hire his technical lead. I introduced him to the lead investor in their seed round. Along the way, I learned how his business worked from every angle: through his customers, his team, and his investors.

When the opportunity came to do an SPV into Glasshouse, it was obvious, I knew exactly who I was backing and why. A no-brainer for Jimmy too, I’d been acting like I was on the team long before the check was significant.

That’s how I earn the right to invest. That’s how I end up in the best deals.

Selfishly, I want my checks to be as big as possible when founders get to that point. I also know not everyone has the time, patience, or The Lighthouse to run diligence the way I do. SPVs with Sydecar let me double down on the founders I believe in and give other investors a chance to participate in deals (and diligence) they normally can’t get in. Sydecar has made it shockingly easy to put meaningful deals together. It takes < 4 hours to set it up, publish the email, host a founder call and get all the investors onboarded and money wired. 

Investing in People, Not Companies

Throughout all of this, I’m just trying to get to know the founder as deeply as possible as a person.

Most early-stage investors say they “invest in founders over business models.” They do, the words are the same, but my version is different. 

Almost every founder I’ve backed has had dinner at my home. I’ve gone to Iceland with founders on retreat, to Bozeman for deep dives, even just 30 minutes down the road for a sleepover where all we did was talk about their business. I’ve done triathlons with some, cried with others, and some of us even say “I love you.”

I’ve met their spouses and kids. I get the daily texts when they land a new customer, a new investor, or just a small win that made their day. I try to be a friend through the highs and the lows, but more than that, I try to be their positive witness. Building a company is brutally lonely. I can’t erase that loneliness, but I can believe in them so deeply that in the moments they lose belief in themselves, they can lean on mine.

That’s why I don’t just want to know what they’re building, I want to know why.

Because the best founders rarely surface their real challenges in polished investor updates. “We need more intros.” “Hiring is hard.” That’s not the truth underneath. The truth, the doubts, the near-burnout moments, the quiet fears they can’t even articulate, only comes out in long, unguarded conversations. And if you’ve taken the time to really know them, you’re the one they’ll open up to.

That’s why I invest in the founder spirit above all else. 

Business models change. Products pivot. But the spirit, the why, does not.

The Bottom Line

So that’s my playbook. Find the best founders. Ask what they need. Build those things. Help first, invest later. And always, always invest in the person.

It’s not complicated. It just takes a willingness to do the work. If more people operated this way, more founders would win. And that’s all I’ve ever wanted.

If you enjoyed this article, feel free to view our prior posts on adjacent topics 

• Why Syndicate Leads Don’t Survive 

• The Syndicate LP Churn Problem 

• What Really Drives Investment Interest in SPVs

Last Money in is Powered by Sydecar

Sydecar empowers syndicate leads to manage their investments more effectively. Organize, manage, and engage your investor network effortlessly with Sydecar’s management and communication tools. Their platform also automates banking, compliance, contracts, tax, and reporting, freeing up syndicate leads to focus on securing deals and strengthening investor relations. Elevate your syndicate operations with Sydecar.

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✍️ Written by Zachary and Alex