Startups

How Pilot charted a course of not raising too much money

Comment

Image Credits: Pilot co-founders Jessica McKellar, Waseem Daher and Jeff Arnold. / Pilot

A few weeks ago, we wrote about fintech Pilot raising a $100 million Series C that doubled the company’s valuation to $1.2 billion.

Bezos Expeditions — Amazon founder Jeff Bezos’ personal investment fund — and Whale Rock Capital joined the round, adding $40 million to a $60 million raise led by Sequoia about one month prior.

That raise came after a $40 million Series B in April 2019 co-led by Stripe and Index Ventures that valued the company at $355 million.

Both raises were notable and warranted coverage. But sometimes it’s fun to take a peek at the stories behind the raises and dig deeper into the numbers.

So here we go.

Jeff Bezos’ investment fund is backing a startup hoping to be the AWS for SMB accounting

First off, San Francisco-based Pilot — which has a mission of affordably providing back-office services such as bookkeeping to startups and SMBs — apparently had term sheets that offered “2x the $40M” raised in its Series B. But it chose not to raise so much capital. 

I also heard that the same investor that ended up leading a now defunct competitor’s $60 million raise first asked to invest $60 million in Pilot as a follow-on to that Series B prior to making the other investment. While I don’t know for sure, I can only presume that what is being referred to is ScaleFactor’s $60 million Series C raise in August 2019 that was led by Coatue Management. (ScaleFactor crashed and burned last year.)

According to CFO Paul Jun: “There were many periods when Pilot turned away new customers and growth capital instead of absolutely maximizing short-term growth…Pilot prioritized building the foundational investments needed for scalability, reliability and high velocity. When it was presented with the opportunity for additional funding towards further growth in 2019, it declined to do so.”

Co-founder and CEO Waseem Daher elaborates, pointing out that the first company that Pilot’s founding team ran, Ksplice, was bootstrapped before getting acquired by Oracle in 2011. (It’s also worth noting that the founding team are all MIT computer scientists.)

“Ultimately, the reason to raise money is you believe that you can deploy the capital, to grow the company or to basically cause the company to grow at the rate you’d like to grow. And it doesn’t make sense to raise money if you don’t need it, or don’t have a good plan for what to do with it,” Daher told TechCrunch. “Too much capital can be bad because it sort of leads you to bad habits…When you have the money, you spend the money.”

So despite what he describes as “a great deal of institutional interest” in 2019, Pilot opted to raise just $40 million, instead of $80 million to $100 million, because it was the amount of capital the company had confidence that it could deploy successfully.

Pilot CEO Waseem Daher tears down his company’s $60M Series C pitch deck

Also, Jun shared some numbers beyond the recent raise amount and valuation.

  • The company has tripled revenue every year since inception, except for 2020 when it doubled revenue.
  • Pilot claims to have had a cash burn of $800,000 per month in 2020 against a starting balance of $40 million.
  • The startup touts a 60% GAAP gross margin. Daher notes: “We feel really good about having long-term unit economics that will work for this business without resorting to offshoring or outsourcing in a way that could compromise quality and compromise relationships.”

Bottom line is companies don’t have to accept all the capital that’s offered to them. And maybe in some cases, they shouldn’t.

More TechCrunch

Struggling EV startup Fisker has laid off hundreds of employees in a bid to stay alive, as it continues to search for funding, a buyout or prepare for bankruptcy. Workers…

Fisker cuts hundreds of workers in bid to keep EV startup alive

Chinese EV manufacturers face a new challenge in their pursuit of U.S. customers: a new House bill that would limit or ban the introduction of their connected vehicles. The bill,…

Chinese EV makers, and their connected vehicles, targeted by new House bill

With the release of iOS 18 later this year, Apple may again borrow ideas third-party apps. This time it’s Arc that could be among those affected.

Is Apple planning to ‘sherlock’ Arc?

TechCrunch Disrupt 2024 will be in San Francisco on October 28–30, and we’re already excited! This is the startup world’s main event, and it’s where you’ll find the knowledge, tools…

Meet Visa, Mercury, Artisan, Golub Capital and more at TC Disrupt 2024

Featured Article

The women in AI making a difference

As a part of a multi-part series, TechCrunch is highlighting women innovators — from academics to policymakers —in the field of AI.

8 hours ago
The women in AI making a difference

Cadillac may seem a bit too traditional to hang its driving cap on EVs. And yet, that hasn’t stopped the GM brand from rolling out — or at least showing…

The Cadillac Optiq EV starts at $54,000 and is designed to hook young hipsters

Ifeel is being offered as part of an employer’s or insurance provider’s healthcare coverage.

Mental health insurance platform ifeel raises a $20 million Series B

Instead of opening the user’s actual browser or a WebView, Custom Tabs let users remain in their app while browsing.

Google Chrome becomes a ‘picture-in-picture’ app

Sanil Chawla remembers the meetings he had with countless artists in college. Those creatives were looking for one thing: sustainable economic infrastructure that could help them scale rather than drown…

Slingshot raises $2.2 million to provide financial services to artists

A startup called Firefly that’s tackling the thorny and growing issue of cloud asset management with an “infrastructure as code” solution has raised $23 million in funding. That comes on…

Firefly forges on after co-founder murdered by Hamas

Mistral, the French AI startup backed by Microsoft and valued at $6 billion, has released its first generative AI model for coding, dubbed Codestral. Like other code-generating models, Codestral is…

Mistral releases Codestral, its first generative AI model for code

Pinterest announced today that it is evolving its Creator Inclusion Fund to now be called the Pinterest Inclusion Fund. Pinterest teamed up with Shopify’s Build Black and Build Native programs…

Pinterest expands its Creator Fund to allow founders

Alex Taub, a longtime founder with multiple exits under his belt, believes it’s time to disrupt the meme industry. “I have this big thesis that meme tech is going to…

This founder says meme tech is the next big thing

Lux, the startup behind popular pro photography app Halide and others, is venturing into video with its latest app launch. On Wednesday, the company announced Kino, a new video capture app…

Kino is a new iPhone app for videographers from the makers of Halide

DevOps startup Harness has shown itself to be an ambitious company, building a broad platform of services while also dabbling in M&A when it made sense to fill in functionality.…

Harness snags Split.io as it goes all in on feature flags and experiments

Microsoft’s Copilot, a generative AI-powered tool that can generate text as well as answer specific questions, is now available as an in-app chatbot on Telegram, the instant messaging app.  Currently…

Microsoft’s Copilot is now on Telegram

HBO’s new documentary, “MoviePass, MovieCrash,” tells a story that many of us know about: how MoviePass, the subscription-based movie ticketing startup, was a catastrophic failure. After a series of mishaps…

MoviePass co-founders speak their truth in HBO’s new documentary 

The watch features a variety of different 3D games, unlocking more play time the more kids move.

Fitbit’s new kid smartwatch is a little Wiimote, a little Tamagotchi

In the video, a crowd is roaring at a packed summer music festival. As a beat starts playing over the speakers, the performer finally walks onstage: It’s the Joker. Clad…

Discord has become an unlikely center for the generative AI boom

After the Wirecard scandal, Germany’s financial regulator BaFin started to look more closely at young fintech startups that wanted to grow at a rapid pace — it’s better to be…

Germany’s financial regulator ends anti-money laundering cap on N26 signups after $10M fine

Among other things, this includes the ability to trace code from source to binary packages across both platforms, single sign-on support and unified project structures.

JFrog and GitHub team up to closely integrate their source code and binary platforms

The company’s public fund disbursement and e-commerce platform makes accepting school tuition and enabling educational enrichment more accessible. 

Tech startup Odyssey goes on journey to help states implement school choice programs

A new startup called Kinnect aims to help people privately save generational memories, traditions, recipes and more. The company’s app, launched this month, lets people create invite-only spaces where they…

Kinnect’s new app aims to help families record and store generational memories

Spotify has hiked its premium subscription in France by an eye-watering €0.13, in response to a new music-streaming tax.

Spotify hikes subscription price in France by 1.2% to match new music-streaming tax

The European Union has taken the wraps off the structure of the new AI Office, the ecosystem-building and oversight body that’s being established under the bloc’s AI Act. The risk-based…

With the EU AI Act incoming this summer, the bloc lays out its plan for AI governance

Solutions by Text, a company that gives people a way to pay their bills and apply for loans via text messaging, has secured $110 million in new growth funding. Edison…

Bootstrapped for over a decade, this Dallas company just secured $110M to help people pay bills by text

Owners of small- and medium-sized businesses check their bank balances daily to make financial decisions. But it’s entrepreneur Yoseph West’s assertion that there’s typically information and functions missing from bank…

Relay raises $32.2 million to help smaller businesses manage their cash flow

When other firms were investing and raising eye-popping sums, Clean Energy Ventures took a different approach. It appears to be paying off.

How Clean Energy Ventures avoided the pandemic bubble and raised a $305M fund

PwC, the management consulting giant, will become OpenAI’s biggest customer to date, covering 100,000 users.

OpenAI signs 100K PwC workers to ChatGPT’s enterprise tier as PwC becomes its first resale partner

Tech enthusiasts and entrepreneurs, the clock is ticking! With just 72 hours remaining until the early-bird ticket deadline for TechCrunch Disrupt 2024, now is the time to secure your spot…

72 hours left of the Disrupt early-bird sale