SaaS Interviews with CEOs, Startups, Founders

Nathan Latka
  • 4.7 (67)
  • Entrepreneurship
  • Updated Daily

What if you knew data behind the fastest growing SaaS companies today? Each morning join Nathan Latka as he spends 15 minutes interviewing SaaS founders. You'll learn how SaaS CEO's launched their startup and grew it into a real SaaS business. SaaS Founders range from bootstrapped to funded, MVP to 10,000 customers, pre revenue to pre IPO.

  1. 6 hrs ago

    Golf Genius: $53M ARR, $10M Self-Funded, Zero VC — Mike Zisman

    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 handicapping platform for golf clubs worldwide. He self-funded $10M of his own money as interest-free debt, did 10 acquisitions before hitting $60M in revenue, and today sits on $14M cash while printing 20% EBITDA margins with 300 employees across the US and Cluj, Romania. You'll learn: Why Mike structured his entire $10M founder investment as debt instead of equity — and how it created a tax shield that paid him back on the way out How the USGA handicapping contract in 2019 transformed Golf Genius from a niche club tool into the infrastructure layer of global golf How Golf Genius went from $0 to $1M ARR in 8 years, then from $1M to $53M in the next 8 — and what the USGA relationship had to do with the inflection point Why 50% of his 300-person team are engineers based in Cluj, Romania — and how that structural cost advantage funds 20% EBITDA while competitors burn cash The exact three-phase acquisition strategy: legacy desktop customer rollups, league expansion, then B2C mobile apps with 8M+ users How Mike negotiated the GolfShot acquisition — and why he forced their entire cap table behind a single LLC before closing Why employees own 60% of the cap table at $53M ARR and how that drives 6-7% annual attrition across the entire company including Romania What Mike would say if a PE firm offered $400M all cash today — and why he says he's more excited about what's next than he's been in years Why he thinks AI will make SaaS companies radically more productive, not obsolete — from a founder whose doctoral thesis in 1977 was already on artificial intelligence The rule of 40 reality at $53M ARR: why growth slows as companies scale and what Mike does to stay above the 10% industry average Connect: YouTube: youtube.com/@NathanLatkawatch Golf Genius: golfgenius.com Founderpath: founderpath.com

    19 min

  2. May 27

    $28M Series A at $100M Val: The Pest Control SaaS Nobody Saw Coming

    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

    21 min

  3. May 21

    He Lost $50/User to Build a $30M ARR AI Empire (Fathom)

    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/

    25 min

  4. May 13

    How 1Mind Hit $1M in 3 Months Selling $100k AI Sales Agents

    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/

    25 min

  5. May 6

    Selling Check for $400M, Now Building a $1.5M ARR AI Startup

    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/

    24 min

  6. Apr 29

    How Flossy Reached $4M ARR With AI Dental Receptionists

    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/

    18 min

  7. Apr 22

    Flip Reaches $12M ARR with AI Voice Support for 250 Brands

    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 and his co-founder Sam pivoted into voice AI. Today, Flip automates up to 90 percent of routine support calls for over 250 enterprise companies and recently raised a $20M Series A at a $100M valuation. You'll learn: How to successfully pivot a failing startup model Why verticalized AI beats horizontal platforms How to implement usage-based pricing at $1.50 per call Why "listen mode" is their best sales tactic How to maintain 75 percent gross margins with AI Why they rejected a theoretical $150 million acquisition offer How to select the right industries for expansion Why competitive B2C markets are best for AI tools Brian started his entrepreneurial journey at Cornell's eLab accelerator. He navigated the near-total collapse of transportation revenue during the pandemic to build a highly efficient business growing 3X year over year. Watch this episode on YouTube: https://youtu.be/gtFt5exyCaI  Connect with Brian:  https://flipcx.com/ Connect with Nathan:  https://founderpath.com/

    25 min

  8. Apr 15

    Kadence Reaches $15M ARR Managing Hybrid Work for Revolut & Boeing

    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 during the pandemic to help companies like Nasdaq, Revolut, and Boeing manage their office space. Today, Kadence serves over 600 enterprise customers. You'll learn: How to manage board expectations during a hard pivot  The exact mechanics of resetting a cap table for new investors Why shifting from SMB to enterprise accelerated revenue How they achieved over 130 percent net dollar retention Why seat-based pricing still works in the enterprise The math behind saving half a billion dollars in leasing costs How launching SpaceOps AI drives multi-product expansion Why high-ticket dinners replaced SEO for customer acquisition Dan started his career managing technology for a church before founding his first IoT business. He moved his family to the Bay Area just before the pandemic forced him to rethink his entire company operations. Watch this episode on YouTube: https://youtu.be/2ySF3YMDcnY Connect with Dan: https://kadence.co/ Connect with Nathan: https://founderpath.com/

    21 min
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What if you knew data behind the fastest growing SaaS companies today? Each morning join Nathan Latka as he spends 15 minutes interviewing SaaS founders. You'll learn how SaaS CEO's launched their startup and grew it into a real SaaS business. SaaS Founders range from bootstrapped to funded, MVP to 10,000 customers, pre revenue to pre IPO.

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