I Sold My Car to Fund My Brokerage, and I'm Not the Only One

I'll admit that for years I read funding announcements and assumed I'd missed some memo about how real founders get started, and I have a feeling a lot of women founders can relate. So I want to talk about money: how businesses in logistics actually get funded, why so little venture capital ever reaches women, and what the rest of us have been doing instead.

How I actually funded my brokerage

I started my brokerage in 2016, and I was lucky enough to have two silent partners support me for the first little while. Even with their help, I blew through both of my credit cards and a line of credit, and eventually I sold my car to make it all work.

I mention the silent partners on purpose, because they didn't show up out of nowhere. They came from my network, from years of working in this industry and building relationships long before I needed anything from anyone. When people talk about funding, they skip straight to banks and investors, but for most of us the first money comes from our own packets and people who already know our work and trust us to follow through. If you're thinking about going out on your own, the relationships you're building right now may become part of your funding plan whether you realize it or not.

The ups and downs nobody posts about

The growth is up and down, and I don't think founders share that part enough, probably because it can be a little traumatizing, and you usually put all of it on yourself. When you've maxed out your own cards to get something off the ground, every slow month feels personal.

There were times I let things slip and we didn't grow, and I'm okay with that now. Sometimes you need to plateau so you can reset yourself and the business. A flat year doesn't mean you failed, and I wish someone had told me that earlier, because I would have spent a lot less time beating myself up about it.

The VC numbers, and the headline that isn't what it looks like

If you believe some of the headlines, 2025 looked like a breakout year for women. PitchBook reported that US female-founded companies raised a record $73.6 billion and captured 27.7% of total venture deal value. Then you read the fine print and find that more than $30 billion of it came from Scale AI and Anthropic raises, and that "female-founded" includes any company with as long as there is a woman on the team.

So, a couple of massive AI deals can make an entire year look like progress while almost nothing changes for the average woman trying to raise her first round. PitchBook itself noted that AI megadeals and later-stage rounds are concentrating capital into fewer, larger deals. At the same time, early-stage funding for women founders actually declined, and fewer early-stage investments means fewer women-founded startups getting a foot in the door to even try.

If we look at companies founded only by women, they got just 1% of total US venture capital in 2024, down from 2% in 2023. Canada is somewhat doing better, since a CVCA (Canadian Venture Capital and Private Equity Association) report showed women-led startups went from 4% of total VC investment in 2021 to 12% by the first half of 2024, but that still leaves most of the money going somewhere else.

So why doesn't the money reach women?

The easy explanation people reach for is that women don't pitch as hard or don't build businesses big enough, except the research doesn't support that. What it points to is how the whole system is set up.

Start with who's writing the cheques. When BCG and MassChallenge ran their study, 92% of partners at the biggest US VC firms were men. In Canada, women accounted for 19.4% of partners at venture capital firms in 2021, which is why we see better/growing numbers in Canada. Investing tends to run on networks and warm introductions, so when the people with the money mostly look alike, the deal flow tends to look alike too.

Then there's what happens if you get in the room to pitch. Researcher Dana Kanze studied nearly 2,000 questions investors asked at TechCrunch pitch competitions and found that investors, regardless of their own gender, asked men questions about potential gains and asked women questions about what could go wrong, and awarded the women less money. Men got asked how big this could get, and women got asked how they planned not to lose everything. It made a real difference: entrepreneurs who were asked promotion questions received twice as much funding as those asked prevention questions. 

A follow-up study found that women-led ventures serving male-populated industries received significantly less funding at lower valuations than women-led ventures serving female-populated industries, while men got similar results no matter which industry they served. In other words, a woman building a freight tech company or a trucking business gets penalized for not "fitting," and a man building the same type of company doesn't. 

Women do more with less, and investors still aren't paying attention

Women also tend to get more bang per buck they do get in funding. BCG and MassChallenge found that startups founded or cofounded by women received less than half the funding of male-founded ones, yet generated 78 cents in revenue for every dollar of funding while the men generated 31 cents.

Part of the reason is that women tend to be more realistic in their financial projections, and in a system that rewards the boldest promise over the most accurate one, being honest can cost you money. I also think that when you've built something on credit cards and a sold car, you learn to make every dollar do three jobs, and that habit sticks with you even once there's more money coming in. That's a better return on a smaller investment, and investors keep passing on it.

What's out there besides VC

Honestly, VC is often not the right fit for most freight and logistics businesses anyway. VC firms make most of their returns from a small number of wildly successful deals, so they're hunting for companies that can grow ten or a hundred times over. A brokerage, a small fleet or a warehouse runs on thin margins and steady cash flow, which makes it a good business but not the kind VC is built to fund.

What works better for most of us is funding designed around how freight actually moves. Factoring is a lifeline if you're waiting 60 days for a shipper to pay and still need to pay your carriers this week and buy fuel. Equipment financing makes sense in trucking because the truck itself secures the loan, so you're not putting your house on the line.

In Canada, BDC has a $50-million Thrive ETA initiative to help women acquire or lead established companies, which is worth a serious look in an industry full of owner-operators and small fleets heading toward retirement. Buying a business that already has customers and cash flow is a completely different risk than starting from zero. There are also investors focused specifically on women, including Backbone Angels, which backs women and non-binary founders, and seed-stage firms like StandUp Ventures and Sandpiper Ventures.

And yes, bootstrapping is still on the list. I did it, I wouldn't recommend doing it the way I did without a plan, but I'd be lying if I left it off.

Ship Happens isn't in the black, and I'm fine saying that

Ship Happens was more of an accident. The brokerage paid the bills, so I started posting on Instagram and LinkedIn, things grew, I built a website with a blog, and when I started featuring women in the industry my own voice grew with it. Having one business fund the other is its own kind of funding model, and a lot more common than people might realize.

Am I in the black with Ship Happens? Not at all. Do I bring in revenue? Yes, of course. It's a different part of our industry, focused on informing and educating, and people sometimes struggle to see how that brings value to their business, which is fair, because education pays off slowly and it's hard to clarify on a budget. I'm lucky to have a network that refers me, suggests ideas, and invites me to attend and speak at events, which is the same thing that got my brokerage off the ground. I'm also super stubborn, and I see the value and the need for more education and better-informed decisions in this industry.

Where that leaves us

VC works for some companies, and good for them. For most of us in logistics, the money came from our own pockets, our networks and whatever we were willing to sell, and knowing why the system works the way it does makes it a lot easier to stop taking it personally and start finding the money that actually fits your business.