Imperfect Company is a podcast from Glitch Capital where Leigh Jasper and Sam Kroonenburg — two founders who've built billion-dollar exits and are going again — sit down with founders to talk about the strategic decisions nobody puts on the pitch deck: the false starts, the bad hires, the pivots, and the unglamorous calls that actually built something real.

In this first episode, Leigh and Sam tell their own stories before the guests arrive.

Sam walks through how A Cloud Guru grew from a 30-pound webcam in a London bedroom to a $2B sale to Pluralsight in six years — funnelling students off Udemy, bootstrapping to $3.5M ARR, raising a quarter of a billion dollars in three weeks to buy his biggest competitor, and the unconventional bet to give the product away free to 50,000 Amazon employees.

Leigh shares the longer, harder road of building Aconex — selling software to construction sites that didn't have internet, surviving both the dot-com crash and the GFC, taking the company public, weathering short sellers, and ultimately selling to Oracle for $1.6B in a deal that made 100 early staff and investors millionaires.

And they get honest about the bad days: every VC saying "no" on a single flight, an IPO collapsing from a Rome hotel bathroom, and two separate pieces of devastating news that both landed while they were at theme parks with their kids.

Now they're back, building AI-native companies — Sam with Cutable and Leigh with Firmable.

In this episode:

• How A Cloud Guru turned Udemy students into direct customers

• Bootstrapping to $3.5M ARR before raising a dollar of VC

• Raising $250M in three weeks to acquire a larger competitor

• Why giving the product away to Amazon employees drove 20–30% of revenue

• Timing the 2021 market top with the Pluralsight/Vista sale

• Selling enterprise software before customers even had internet

• Surviving the dot-com crash and raising during the GFC

• The realities of being a public-company CEO and the Oracle exit

Recommended in this episode:

• Spin Selling — Neil Rackham

• The Challenger Sale

• The Art of Closing the Sale — Tom Hopkins

• Zig Ziglar's sales classics

• The One Minute Manager — Ken Blanchard & Spencer Johnson

• The Five Dysfunctions of a Team — Patrick Lencioni

Next episode: Mark Finn, founder of Roller.

Follow or subscribe so you don't miss an episode.

→ Follow Glitch Capital on LinkedIn.
→ Connect with Leigh
→ Connect with Sam 
→ Got a question for Leigh & Sam, or a founder story we should cover? Send it to them on LinkedIn and we'll answer listener questions on the show.

Imperfect Company is a new podcast from Glitch Capital where Leigh Jasper and Sam Kroonenburg, two founders who’ve built billion dollar exits before and are going again, sit down with founders to talk about the strategic decisions nobody puts on the pitch deck — the false starts, the bad hires, the pivots that needed to be made, and the unglamorous decisions that actually built something real.

This is the trailer. Here's what the show is, who it's for, and why we're making it.

New episodes coming soon. Follow / subscribe so you don't miss episode one.

• Follow Glitch Capital on LinkedIn here

• Subscribe to Imperfect Company on YouTube here

• Connect with Leigh here

• Connect with Sam here

• Got a question for Leigh & Sam? Send it to them on LinkedIn and we'll answer listener questions on the show with our guests.