At the end of 2019, Lawtrades’s bank balance was down to $20k.
People were getting value from our platform, but we were struggling to convert that
value into a healthy balance sheet. Investors were wary of our niche after Atrium shut
down, so we had little choice but to go into survival mode—cutting 80% of our staff,
and even, at one point, putting expenses on personal credit cards.
Most companies in our position would have gone knocking on VCs’ doors, looking for
capital to bridge the gap to profitability.
But we felt we could preserve our equity, stay resourceful, and elbow-grease our way
across the chasm.
First, we pivoted, shifting focus from small-to-midsize businesses (SMBs) to
hypergrowth tech startups. That brought its own slew of challenges, and a brush with
bankruptcy that we narrowly avoided. But ultimately, we managed to hack our
revenue, taking it from $70k/mo to $700k/mo.
Here’s how we did it, step by step, and the lessons we learned along the way.
In the beginning, Lawtrades tried to serve every type of client. Mostly, this meant
SMBs who couldn’t afford full-time legal teams. Unfortunately, it also meant:
more prospects we had to nurture, hiking our customer acquisition cost.
more fronts than we could afford.
Taking a cue from Peter Thiel, we realized that competition was for losers, and that
the only way forward was through our most profitable customer segment: hypergrowth
tech companies, often pre-IPO, whose general counsels (GCs) needed ongoing support.
We fired everyone who didn’t fit that niche, and quickly became a go-to tool for
companies like Cruise and DoorDash.
Lesson #1: Riches are in niches.
Having identified our niche, we naturally started learning a lot about it. What
problems did GCs commonly face? How did they solve them? What trends were
impacting the space, and how could legal teams stay ahead of them?
To collect our insights, we created a Substack newsletter, Forward GC. Over time, this
platform, but as thought leaders in the niche.
earned endorsements from prominent brands like DoorDash.
effective—especially when it brings in repeat customers.
Lesson #2: As Paul Graham said, “It’s better to make a few users love you than a lot
The one great thing about serving SMBs was that they paid quickly. Our newer, larger
customers often worked on 30-, 60-, even 90-day billing cycles. Given that we pay our
lawyers every two weeks—Lawtrades is fundamentally about economic empowerment
on the supply side—that meant our outflow outpaced our income.
The more hypergrowth customers we attracted, the more we grew—and the faster we
lost cash. This is where we got down to $20k, where my co-founder and I paused
our salaries, and we where had to go into survival mode.
Lesson #3: Don’t grow broke. It’s not always within your control, but avoid it if you possibly can.
Desperate times called for desperate measures:
directly—both inconvenient and suspicious.
much as 10-20%—near-impossible to justify.
prompted some (very) angry words with Amex.
Each of these steps bought us some time, but never sustainably. We couldn’t keep
borrowing badly, and Amex threatened to shut down my account
Again, this is where a lot of companies would turn to VC. But we simply believed we
didn’t have to—we had legitimate receivables, it was just that they were taking a long
time to come in on companies’ billing cycles. Shouldn’t there be a way to leverage
those receivables to get capital that would let us pay our supply side, and make it to
our next growth stage?
Just in the nick of time, we learned about a new debt option that let us do exactly that.
Lesson #4: Before you default to VC, consider new debt options. As a founder, the
most valuable optionality you have is the equity you haven’t sold, the dilution you
By a stroke of luck, we learned about a company that provides upfront capital based on
receivables. After a few conversations, Capchase agreed to take a chance on us, freeing
us up to:
got paid quickly for the work they did, without having to wait out long billing cycles.
With more cash on hand to spend on customer acquisition, receivables continued
to grow. More receivables unlocked more debt, which allowed us to acquire more
customers. And so on.
when times were tough, we probably could have raised at a $30-$40M valuation.
But because we waited, we were able to revisit fundraising with an $80M valuation,
ultimately raising $6M, diluting less than 10% equity.
By this point, VC was a way to diversify our revenue streams, thereby de-risking our
CapChase credit line.
Lesson #5: Use VC for Research & Development—innovation—not as a Sales &
Marketing or General & Administrative holdover.
The level of effort and maneuvering it’s taken to turn our growth from a liability into
an asset has been incredibly illuminating. For startups, it’s not as simple as finding
customers or even finding the right customers. There’s an enormous level of nuance
even within those objectives.
We are often given the advice that “debt is bad.” We’re told to avoid it at all costs. But
with the right partners and plan in place, debt is a powerful mechanism to grow
without giving up equity. In our case, we had customers coming in and expenses under
control—it was a cashflow problem. And debt solved it.