Conversations with founders who nearly lost everything before building something unforgettable.
The moments no one posts on LinkedIn. New story every Tuesday.
Featured episode
The night we had $117 left.
Ep 042 · Guest
Maren Ostroff
Founder, Loomwork · $18M ARR
She missed payroll on a Thursday, wired her rent money on Friday, and closed a Series A three weeks later. This is how it actually happened , hour by hour.
Key takeaways
- The 4-line email that saved the round
- Why she stopped hiding the runway from her team
- The customer call she almost didn't make
Said out loud
“I almost lost payroll three times.”
“We had $117 left.”
“I mortgaged my house.”
“Our biggest customer left.”
“The board asked me to step down.”
Featured guests
Founders who survived the part they don’t talk about.
Maren Ostroff
Founder, Loomwork
David Kwon
CEO, Northstar Mfg
James Auber
Founder, Silt AI
Naomi Rhee
Founder, Rhee & Co
Priya Shah
CEO, Fable Goods
Marcus Vale
Founder, Vale Holdings
Maren Ostroff
Founder, Loomwork
David Kwon
CEO, Northstar Mfg
James Auber
Founder, Silt AI
Naomi Rhee
Founder, Rhee & Co
Priya Shah
CEO, Fable Goods
Marcus Vale
Founder, Vale Holdings
About the show
The best businesses aren’t built from perfect stories. They’re built from setbacks.
Almost Broke exists to tell the stories no one posts on LinkedIn. Every guest shares the moments they thought everything was over , and how they found a way through.
Not flashy. Not motivational. A place where founders tell the stories they normally never share.
Your host
Two failed companies. One that finally worked. Chris started Almost Broke because the podcasts he needed at 3am didn’t exist. Now he interviews the founders he wishes he could have called.
“Success stories are edited. I want the unedited version.”
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Upcoming guests
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Coming Soon
Ellery ZhangFounder, Halcyon Studio
Dec 3
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Tomás HerreraCEO, Costa Foods
Nov 25
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Lena WhitfieldFounder, Basewell
Nov 19
Scheduled
Ravi BhattCEO, Ledger AI
Dec 10
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