volume 004: how to raise capital when your savings won’t cut it
A first-hand account on how to break into the fundraising ecosystem to grow your brand.
I was 24 years old when we started Halfdays. I had no clue how to launch a brand, let alone any knowledge of how to build a financial model or fund the idea. But with a mix of serendipity, scrappiness, and the right people at the right time, I found a path forward — one that meant bringing on outside capital to get things off the ground.
Let’s get one thing straight: raising capital is a path — not the path. It’s not right for everyone. If you’re not aiming for a $100M+ business, not planning to sell or IPO, and just want to grow something sustainable and profitable — that’s more than okay, and it’s arguably the best way to go if you can swing it.
However, not everything can be bootstrapped. Especially if you don’t have the capital. So if you do choose to raise, just know: it’s not free money. It’s the kind with strings — and they’re long, tight, and usually come with quarterly (or monthly if you’re really lucky) check-ins.
You need to ask yourself:
Am I trying to build a $100M+ business?
Am I willing to give up ownership in exchange for speed?
Am I ready to answer to someone else about how this thing grows?
If the answer is no — amazing. Own that. Build a leaner model. Keep more equity. Sleep better at night.
If the answer is yes — keep reading.
So, how do you get access to capital?
In reality, most of us don’t have friends casually sitting on extra cash to fund someone else’s dream.
Luckily there are dozens of ways to raise money: pre-orders, crowdfunding, bank loans, friends and family, angel investors, venture capital, convertible notes, SAFEs. I won’t break each one down here… though I’m sure ChatGPT would love to give you a crash course.
Here’s what I’ve learned firsthand about what it takes to actually get in the room, and what to know before you say yes to the money…
Know what game you’re playing before you jump in.
A lot of people talk about “raising capital” like it’s the natural next step in starting a business. It doesn’t have to be. It’s a tool for scale and a bet on hyper-growth, but when you accept that money, you’re agreeing to play by a new set of rules.
The most important one? Return the investment.
And not just return it… multiply it (think: 10x or more). That’s what investors are signing up for. Most aren’t in it for slow and steady (with a few rare exceptions). They’re looking for category winners, big outcomes, and ideally, liquidity in five to ten years. Maybe sooner. Their endgame is an acquisition, a secondary sale, or an IPO. Anything else just doesn’t work for how their funds are structured — so don’t take it personally!
Equity comes at a cost. Choose wisely.
At Halfdays, we’ve raised capital from angel investors and venture funds. And while I’ve had a positive experience overall, I don’t romanticize it. Fundraising is high-stakes, high-pressure, and full of hard conversations about what your business is worth, where it’s going, and how fast it can get there.
The first thing to understand: when you sell equity, you’re giving up part of your company. Forever.
And that decision isn’t just financial — it’s deeply relational. Because once someone is on your cap table, they’re on the ride with you. And they’ll stay there until one of three things happens:
They sell their shares in a future fundraising round
You sell the company
You go public
This is not a situationship. It’s legally binding. So if you’re going to raise, make sure you trust the people you’re getting in bed with. Do they understand your business? Do they align with your vision? Can they ride the ups and the inevitable lows?
One of the best pieces of advice I’ve ever received:
“Never take money from someone who really needs it back.”
Here’s what this actually means: if an angel investor wants to write you a $25K check, but it’s clearly a financial stretch for them, think twice. The hard truth is most startups don’t work. Early stage investing is one of the riskiest types of investing. So if someone is counting on this one deal (read: your company!) to deliver their big return? That’s a lot of pressure — and can cost you more than equity (cough, cough: peace of mind).
You need to find an “in”.
Most of the time, it starts with someone you know. Or someone they know. Or someone they know. You don’t need to be besties with a VC — but you do need a warm intro. And that almost always comes from a few degrees of separation.
For us, that “someone” was Karelle — who ultimately became our third co-founder.
Kiley and I had been heads-down on Halfdays for about six months when a mutual connection introduced us to Karelle — a total stranger who, somehow, was also working on a ski brand. Different city, same idea. The timing was uncanny, and looking back, it was one of those universe moments that changed everything.
She ended up joining us pre-launch, and things moved fast after that. Karelle was the catalyst we didn’t even know we needed. She was someone on our side who could help make some initial intros — but let’s be clear: the work was still ours to do. I built the pitch deck, took hundreds of investor calls, hustled to get rounds closed under tight timelines, and received an absolutely absurd number of no’s. (More on that in a minute..)
While I’d like to believe the Law of Attraction brought Karelle, Kiley, and me together (and maybe it did?), your “in” might look a little different. If you don’t have a ready-made connection, here are a few ways to start building one:
LinkedIn. I know, I know — but seriously, don’t underestimate it. Look for people who’ve invested in companies like yours, and send them a message. Keep it short, clear, and confident. Ask for 15 minutes to share what you’re building. One conversation really can lead to the next.
Advisors. There are people out there who will offer up their Rolodex in exchange for equity. Sounds intense, but it’s real — and it works. Think: 0.5–1% equity in exchange for a year or two of guidance, specifically to help you raise or open doors you can’t on your own (yet).
Co-founder. If you’re riding it out solo, it might be worth considering a partner — especially someone who’s done this before. A great co-founder can bring not only experience but also access to investors, advisors, and strategic intros you might not have otherwise.
Always ask for more intros.
I’ve lost count of the rejections I’ve gotten over the years while raising capital…
“We don’t do apparel.”
“How’s this different than Patagonia?”
“Come back when you have revenue.”
Fun! But the truth is — after a while, the no’s start to sting less. You hear enough of them and they sort of roll off your back.
Those weren’t the glamorous meetings, but they ended up being some of the most important. Because even if they didn’t cut a check, they usually pointed me to someone who might.
If you take one thing from this newsletter: never leave a meeting without asking for intros. That’s how five meetings turn into 50. And it’s how you start turning a few loose connections into your own big, beautiful network.
Follow the ground rules.
There’s an unspoken code of conduct in the funding ecosystem. If you don’t take these seriously, I promise you will learn them the hard way like I did:
Double opt-in, always! Don’t introduce anyone unless you’ve cleared it with both parties first. That’s just good etiquette, plain and simple.
Be relentless, but not obnoxious. You can be persistent and still respectful. Don’t send five follow-ups in a row. Read. The. Room.
Be specific with your asks. Don’t say “Can you intro me to 20 investors?” Instead: “I saw you’re connected to [Angel Name] and [VC Name] on LinkedIn. Would you be open to forwarding a short blurb from me to see if they’re open to connecting?”
The bottom line: Raising capital isn’t glamorous. It’s hard and emotional. It will give you thick skin no matter the outcome. If someone wants to give you money, consider it a relationship you’re signing up for. And if you’re not building a business designed for scale, it might not make sense for you at all.
But if you are.. then go find your “in.” And build your own way from there.
Now, per usual, what I’m shopping…
If you know me, you know I have an unhealthy obsession with sunglasses. Here are a few I’ve been eyeing —
Over & Out,
–Ari
PS — if you want to chat more about fundraising, getting intros, or just general startup advice, you can book time with me here!