What it’s like to bootstrap sales

Every few weeks, I sit down with my dear friend Danny at our favorite local spot, Arlequin Cafe. As friends do, we cover many topics, but we always find ourselves back on the topic of sales, and more specifically, how to properly build sales at the various companies where we invest and advise.

Last week, sales came up again, naturally. This time we went holistic on the topic. We ultimately agreed there is knowledge gap for founders when it comes to bootstrapping sales — building sales from the ground up.

A bit of history on how we came to this conclusion. Back in the pre-Snapchat era, we were comrades-in-arms at Groupon and went through the hyper growth phase with the company, pre and post IPO. We’ve since built sales at half a dozen companies and in all scaled businesses from $0 to $10M and $1B to $2B in revenues, closing deals from $2K to $2M (tooting our own horns a bit now). Together, and in the past few years, we’ve advised over 100 companies on the same topic.

We’ve bootstrapped sales ourselves, scaled up and down, hired and fired, built complimentary business units like support, sales and business development, sales operations, and everything else in between that’s sales related. We’ve been lucky to come out of those experiences alive only bearing scars and having learned lots of lessons.

So we’ve decided to share our experiences in hopes it helps founders. Our goal is to get in the weeds and share actionable, meaty instructions on how to bootstrap and scale sales.


Bootstrapping sales is about properly building your revenue initiative for future scaling, not about hacking relationships, pillaging markets, or speedracing through prospects.

Building a real business, one with the sole purpose to serve, delight, and provide meaningful value to its customers, requires building a real sales engine.

We believe success in sales comes from following the scientific method. Sales is one continuous experiment and you can’t run an experiment without a process. Sales is more than just hacks or expectations that a good enough product will sell itself. Whether you’re a first-time founder with minimal customer traction, a multiple time technical founder forced into a position to sell for the first time, the first sales hire or just a sales nerd, we are writing for you.

Over the next few months, we’ll deep-dive into bootstrapping sales. Specifically, we’ll cover: sales philosophy, developing customer profiles, lead generation, script writing, prospecting, frameworks for qualification, conversion expectations, metrics, and reporting, sales tools, sales recruiting and training, and of course, closing and winning.

To keep things actionable and/or if you just cannot wait to kick-start your revenue machine: contact Danny for help bootstrapping or scaling sales and Nima if you’ve been bootstrapping so far and now thinking about raising capital.