SaaS Interviews with CEOs, Startups, Founders

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 from 2019 to 2020, raised just $5M over two rounds, then closed a $28M Series A at a $100M valuation in 2025, the same year he crossed $10M ARR.
You'll learn:
— Why PestShare's revenue model is structured like a warranty, and why that makes it nearly impossible to churn
— The difference between contracted ARR and live ARR, and how that gap almost killed their valuation story 
— How embedding into the lease instead of selling direct to residents creates structural GRR that VC-backed competitors can't replicate
— What it actually took to raise at 10x ARR from an investor that only backs 9 companies at a time
— Why Justin's Series A investor pushed him to take $3M in personal secondary and why he says it made him take bigger swings 
— How IGP's PE background forced a full COGS and gross margin rebuild right after closing the round
— Why "if you don't see pests it means the product isn't working" is the exact wrong way to think about pest control retention
— How PestShare went from $1M (2022) to $5M (2024) to $10M (2025), doubling every year with under 1x ARR in prior capital raised
— What property managers actually pay vs. what residents pay and how PestShare navigates that split without losing either side
— Why Justin chose a hyper-concentrated, low-profile fund over a brand-name VC, and what they got in return
 
Connect:
YouTube: youtube.com/@NathanLatkawatch
PestShare: pestshare.com
Founderpath: founderpath.com

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 against giants like Zoom, Otter, and Firefly. Instead of playing the traditional VC game, he gave the product away, lost $50 per user, and built an absolute rocket ship that dominates through bottom-up distribution.
You'll learn:
— Why purposely losing $50 per user per month was the ultimate growth hack.
— The 5-step framework to sequence risk (Retention -> Onboarding -> Acquisition -> Referral -> Monetization).
— How to hit $100k MRR in your first 30 days of monetization.
— Why Richard hired three enterprise salespeople before writing a single line of code for the premium product.
— The exact strategy to gamify fundraising by reserving 15% of your Series A for your users.
— Why open data, MCP servers, and local agents are replacing walled-garden SaaS models.
— How to scale to $30M ARR by pricing bottom-up teams at $25 per seat.
— The reality of stepping down as CEO from a $10M ARR company after 18 years.
 
Watch this episode on YouTube: https://youtu.be/UavacWr2jbQ 
Connect with Richard:  https://fathom.ai/
Connect with Nathan:  https://founderpath.com/

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 using flat subscription pricing instead of metered models. 
- The unit economics of replacing 89 SDRs and 19 sales engineers with a single custom agent. 
- How they maintain 80 to 90 percent SaaS margins while running heavy LLM operations. 
- The strategy behind 1Mind's 600 percent year-over-year growth rate. 
- Why most enterprise customers purchase a second AI agent within 90 days of going live. 
- How 1Mind uses their own AI agent to source 78 percent of their eight-figure pipeline. 
- The reality of managing founder dilution and secondary sales after building a $380 million business. 
- Why AI agents are expanding past chat interfaces and joining live Zoom calls to run product demos.
Amanda is a three-time entrepreneur who previously founded and served as CEO of 6sense, scaling the company through multiple funding rounds and a $380 million valuation before stepping down.


Watch this episode on YouTube: https://youtu.be/lFX0n3uYTkw 

Connect with Amanda: https://www.1mind.com/
Connect with Nathan: https://founderpath.com/

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 an accounting headcount.
- Why the company raised a $15 million seed round just to build their initial data architecture.
- How they landed a $300,000 engagement in their first year of going to market.
- The exact strategy Ahikam used to distribute $25 million in retention bonuses during a past acquisition.
- Why building a proprietary graph database is the only way to prevent AI hallucinations in finance.
- How SafeBooks scaled to 15 paying enterprise customers.
- The economics of automating the quote-to-cash process across disparate CRMs and ERPs.
- How to manage founder dilution while building a venture-backed tech company.
Ahikam is a veteran fintech executive who previously co-founded Check, which he scaled and sold to Intuit in 2014 for nearly $400 million, creating over 10 millionaires in the process.
Watch this episode on YouTube: https://youtu.be/JQA3RX9PsHw
Connect with Ahikam:  https://safebooks.ai/
Connect with Nathan:  https://founderpath.com/

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 millions, Miles raised a $15M Series A for a dental discount plan. When the market shifted, he pivoted the company entirely to voice AI, made hard cuts to the team, and found explosive product-market fit. Today, Flossy is growing 60 to 70 percent month over month.
You'll learn:
Why vertical AI agents beat general tools like Intercom 
How to sell $500/month software to PE-backed roll-ups 
The reality of firing 30 people to save a company's burn rate 
How a $1 million breakup fee saved a past acquisition deal 
Why they rejected a theoretical $40 million buyout 
The math behind adding $100,000 in new ARR each month 
How they used a $3M seed round to survive 2020 lockdowns 
The mechanics of multi-location enterprise SaaS deals
Miles is a seasoned operator who previously built and sold Equal to Everyday Health for $30M, and Silver Sheet to AMN Healthcare, before diving into the dental tech space.
 
Watch this episode on YouTube: https://www.youtube.com/watch?v=U2RAjHVdHZM 
Connect with Miles: https://www.flossy.com/
Connect with Nathan: https://founderpath.com/