Building a company is messy. Most of it never makes the highlight reel. Imperfect Company is a podcast from Glitch Capital where Leigh Jasper and Sam Kroonenburg, two founders who've built billion-dollar exits before and are going again, talk about the strategic decisions nobody puts on the pitch deck.

This episode's guest is Dom Pym, co-founder of Up, the fastest-growing bank in Australian history and one of the only neobanks still standing, which was acquired by Bendigo and Adelaide Bank.

He started his first company at fourteen, became SAP's youngest-ever employee at nineteen, and has since founded twenty-two companies, including a record label, the world's first online grain exchange, and Pin Payments.

They go deep into the two exits that bookend his career.

The first was the acquirer of his grain exchange. Within five weeks, the acquirer was firing staff, the earn-out tranches never came, and the lawsuits followed. Five years later, and $25 million in combined legal costs later, the judgment ended in a nil result, with no costs awarded to either party. Dom had mortgaged the family home five times to make payroll.

Everything about the second exit was engineered so that it could never happen again. Cash up front, with the entire earn-out negotiated to be paid at completion.

Plus the product philosophy behind Up. The three buckets of requirements and why they deliberately overweighted the features customers never ask for.

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→ Got a question for Leigh & Sam, or a founder story we should cover? Send it to them on LinkedIn, and we'll answer listeners' questions on the show with our guests.

Building a company is messy. Most of it never makes the highlight reel. Imperfect Company is a podcast from Glitch Capital where Leigh Jasper and Sam Kroonenburg, two founders who've built billion-dollar exits before and are going again, talk about the strategic decisions nobody puts on the pitch deck.

This episode's guest is Sam Senior, founder of Monarch — a kid from Hervey Bay who's been building in San Francisco for eleven years. He's pivoted the company twice.

They go deep into how those pivots actually happened: why the original marketplace product had a working supply side and a demand side that never materialised, and how an intern's suggestion to sell the same product to Zendesk's own sales reps made more money in two weeks than the previous two years had.

What survived both pivots was the underlying technology, which is now Monarch: agents that map everything a piece of enterprise software can do, then run workflows fifty steps long across ten different products.

Plus Sam's expectations as a leader, including how everyone needs to automate ten per cent of their job every month; why he pays for his executive team to be in therapy and would rather be described as kind than nice; and the case for building in Australia right now. Plus how Australia has an eighteen-to twenty-four-month enterprise AI adoption gap.

New episodes every fortnight. Follow/subsecribe so you don't miss an episode.

→ Subscribe to the Imperfect Company Newsletter 

→ Follow Glitch Capital on LinkedIn

→ Subscribe to Imperfect Company on YouTube

→ 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 listeners' questions on the show with our guests.

Building a company is messy. Most of it never makes the highlight reel.

Imperfect Company is a podcast from Glitch Capital where Leigh Jasper and Sam Kroonenburg, two founders who've built billion-dollar exits before and are going again, talk about the strategic decisions nobody puts on the pitch deck.

In this episode, the two of them talk about the thing they've each now done twice: taking an Australian company into the United States. Leigh did it with Aconex and is doing it again with Firmable, which has just landed in San Francisco. Sam did it with A Cloud Guru out of Austin and is doing it again with Cuttable, which has just opened in New York.

They go deep on the decisions they're making a: why you transplant someone from the home team instead of hiring a country manager, how Aconex only found growth in the US after abandoning most of the market, picking a city for time zones and customers rather than prestige, when to flip the TopCo, and why Leigh thinks a founder eventually has to be the one on the ground.

Plus the American sales culture Australians tend to skip (President's Club turned out to be the best money ever spent), the coaching Sam got walking out of a US sales call — "you've got to be more American" — and the double discount that costs Australian founders: they understate their traction, then US VCs discount it again on the assumption they're being oversold.

New episodes every fortnight. Follow/subscribe so you don't miss an episode.

→ Subscribe to the Imperfect Company Newsletter 

→ Follow Glitch Capital on LinkedIn

→ Subscribe to Imperfect Company on YouTube

→ 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 listeners' questions on the show with our guests.

Building a company is messy. Most of it never makes the highlight reel.

Imperfect Company is a 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 calls that actually built something real.

In this episode, Leigh and Sam sit down with Didier Elzinga, co-founder of Culture Amp. Didier spent 13 years in Hollywood visual effects — working on Lord of the Rings, Harry Potter and Superman, rising from sysadmin to CEO of Rising Sun Pictures by 26 — and then walked away from it all to build a SaaS company in, of all things, people and culture.

They go deep on the decisions that don't make the deck: splitting company equity four ways, the two failed pivots before employee engagement stuck, why Culture Amp refused to pay sales commission until $100M in revenue, and the hiring "heresies" Didier still swears by.

It's a candid conversation about the worst days too. What actually holds a team together: storytelling, conviction over correctness, and a leader's job to absorb fear rather than project it. They close by noting where AI is taking work now and the "imagination asymmetry" Didier thinks is the real gap for most companies.

New episodes every fortnight. Follow/subscribe so you don't miss an episode.

→ Follow Subscribe to the Imperfect Company Newsletter 

→ Follow Glitch Capital on LinkedIn

→ Subscribe to Imperfect Company on YouTube

→ 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 with our guests.

Building a company is messy. Most of it never makes the highlight reel.

Imperfect Company is a 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 calls that actually built something real. In this episode,

Leigh and Sam talk through what’s actually different about building in an AI-native world — and what hasn’t changed at all.

They get specific about how AI shifts team shape (engineers running ahead of PM/design), why outcome “harnesses” matter more than prompts, and why taste and coherent UX might be the real bottleneck.

They also zoom out to the investor lens: if software is cheap and fast, what’s defensible now? Data, networks, compliance, and “hard things” (sometimes even hardware) start to look more interesting — and simple feature velocity starts to look less like a moat.

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

→ Follow Subscribe to the Imperfect Company Newsletter 

→ Follow Glitch Capital on LinkedIn

→ Subscribe to Imperfect Company on YouTube:

→ 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 with our guests.

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 their journey: the false starts, the bad hires, the pivots, and the unglamorous calls that happen when you build at scale.

This episode: Mark Finn, co-founder of Melbourne-based Roller, the venue management platform that is the market leader in the US, running thousands of theme parks, trampoline parks, museums and attractions around the world, with roughly 70% of its business in the US.

Mark and his brother Luke started out building a booking system for Melbourne jazz clubs when until an inbound email from a Geelong adventure park revealed a far bigger opportunity: an entire leisure and attractions industry still running on legacy, on-prem software.

Mark takes Leigh and Sam through the tactical calls: how he earned a bigger TAM numbers and won by owning a niche first, how a 20 year old backpacker from his team cracked the UK, how they focused on anchor customers in the US early and why they embedded payments during COVID, using M&A to acquire competitors and roll their customers onto Roller, staying capital-efficient through the zero-interest-rate years, and building a US team when "Americans aren't Australians." This is the honest version of company building. Imperfect, on purpose.

Chapters

00:00 — From Melbourne jazz clubs to a US market leader

1:20 From Macquarie & PwC to building with his brother

6:30 Cracking the UK with one salesperson and £30k

8:00 on the ground in the US: Coney Island & Sky Zone

13:18 Bootstrapping, angels and the Australian VC "no"

16:40 Why big TAMs are a trap: win the niche, earn the right to expand

24:14 Embedding payments — and moving into capital & lending

34:20 The worst day: 23 March 2020

49:00 M&A as a growth engine: three acquisitions

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

→ Follow Glitch Capital on LinkedIn.

→ Subscribe to Imperfect Company on YouTube:

→ Connect with Leigh:

→ Connect with Sam:

→ Connect with Mark Finn:

→ Learn more about ROLLER here.

→ 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 with our guests.

Building a company is messy, and most of it never makes the highlight reel.

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:

Recommended in this episode:

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.

Building a company is messy. Most of it never makes the highlight reel.

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.