Top Founders

How do you build a $10M business by teaching robots to write handwritten notes with real pens, and do it with zero outside investment for 12 straight years?

David Wachs sold his text message marketing company for eight figures in 2012, started Handwrytten the next day, and has bootstrapped it to 20...

How do you go from a pricing experiment inside a failing product to $3.6 million in annual revenue with 10,000 customers — in under two years and with zero paid marketing?

Eugene Cheah is the co-founder and CEO of Featherless.ai, the largest open source LLM inference provider on Hugging Face....

How do you build a $15M revenue business by teaching autonomous drones to find missing sneakers in warehouses, and get customers to more than double their spend every single year?

Sankalp Arora is the founder and CEO of Gather AI, a physical AI company that uses autonomous drones and computer visio...

How do you go from $10,000 left in the bank and a down round to $100 million in annual revenue — without ever seriously considering quitting?

Krenar Komoni is the founder and CEO of Tive, a hardware-plus-SaaS company that tracks shipments in real time across trucks...

How do you build a $53M ARR software company, stay profitable for eight straight years, and give 60% of the cap table to your employees — without ever taking a venture check?

Mike Zisman is the founder and CEO of Golf Genius, the dominant tournament management and ...

How do you build a $100M SaaS company by charging apartment residents $5 a month to keep rats out of their bedroom?

Justin Clements is the co-founder and CEO of PestShare, an on-demand pest control platform embedded inside property management software. He bootstrapped fr...

How do you go from 0 to $30 million in ARR in just 3 years while purposely losing money on every single free user?

Richard White is the founder and CEO of Fathom, a free AI meeting assistant used by hundreds of thousands of professionals daily.

After running UserVoice for nearly two decades, Richard entered the hyper-competitive AI transcription war again...

How do you hit $1 million in contracted revenue in three months and achieve 211% net dollar retention in your first year?

Amanda Kahlow is the founder and CEO of 1Mind, an AI platform building go-to-market superhumans that replace SDRs, AEs, and sales engineers.

You'll learn:

- How to sell AI software for $100,000 to $400,000 usi...

How do you build a $1.5 million ARR enterprise AI platform after previously selling a fintech startup for nearly $400 million?

Ahikam Kaufman is the CEO of SafeBooks AI, an agentic data automation platform for the office of the CFO.

You'll learn:

- How to charge $125,000 ACVs by pricing against the cost of ...

How do you survive shutting down during the pandemic, pivot a heavily funded business model, and rebuild a team of 8 into a $4M ARR AI powerhouse?

Miles Beckett is the CEO of Flossy, a verticalized AI receptionist that automates patient booking and engagement for dental practices.

After successfully building and exiting two previous startups for tens of m...

How do you pivot a banned college ridesharing app into a voice AI company handling 300 million customer service calls?

Brian Schiff is the co-founder and CEO of Flip, a verticalized AI voice assistant that automates customer service calls for transportation, retail, and healthcare brands.

After realizing their Cornell ridesharing app was a dead end, Brian...

How do you completely reboot a dying hardware startup, restructure a heavy cap table, and pivot into a SaaS product doing $15M ARR?

Dan Bladen is the co-founder and CEO of Kadence, a workplace operations system coordinating people and spaces for hybrid work.

After realizing his wireless charging startup was a "vitamin, not a painkiller," Dan pivoted durin...

How do you build a construction SaaS to $2M in revenue with just $500K raised and get 95% of growth from SEO?

Hmayak Tigranyan is the founder and CEO of Buildern, a construction management software platform serving around 300 customers and generating roughly $2M in revenue today. The company helps residential and commercial builders manage finances and workflows, and it is doing about $160K in m...

How do you grow an AI phone system to 5,000 customers and roughly $3M ARR in under two years while still aiming for $10M in revenue this year?

Jeremy Goillot is the founder and CEO of The Mobile First Company, which launched Allo as its first product. Allo is an AI phone system and dialer for small businesses, now serving around 5,000 customers with average revenue above $160 per month and a goal of reac...

How do you turn $200K into a $9.7M ARR SaaS company with a $100M valuation by buying IP instead of building from scratch?

Joey Gilkey is the founder of TitanX, a sales intelligence platform generating $9.7M ARR after launching in 2024. The company serves enterprise sales teams with contracts ranging from $24K to $250K annually, with its largest deals exceeding seven figures.

What m...

How do you grow a customer support SaaS to over 1,000 customers and $10M–$25M in ARR in one of the most crowded software categories, without trying to outspend the giants on marketing?

In this episode, Nathan sits down with Grant Stanis, CEO of TeamSupport. The company provides B2B customer support software used by more than 1,000 companies and generates between $10M and $25...

How do you rebuild a declining cybersecurity company into a $70M revenue platform with ~$25M EBITDA after buying it back for under $10M, while scaling primarily through acquisitions and debt instead of venture capital?

Gary Guseinov is the CEO of Realdefense, a consumer cybersecurity and privacy platform that generates roughly $70M in annual revenue with $20–25M in EBITDA. Gary originally founded t...

How do you build an AI SaaS company to $1M+ ARR with just a few dozen customers and raise a Series A at a 20x+ revenue multiple while competing against general-purpose AI tools?

Tal Kirschenbaum is the Co-Founder and CEO of Ledge, an AI-native financial close platform helping finance teams automate the month-end close process. Just three years after writing the first line of code, Ledge has reached $1M+ ...

How do you turn a failed public ecommerce company into a $5M ARR enterprise SaaS platform serving ~$2M+ contracts — while rebuilding with capital efficiency after bankruptcy and avoiding the growth-at-all-costs playbook?

In this episode, Nathan sits down with Jared Yaman, co-founder of Spresso and former founder of Boxed, the bulk ecommerce company that scaled to $187M in re...