SaaS Interviews with CEOs, Startups, Founders

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 [https://youtu.be/lFX0n3uYTkw] Connect with Amanda: https://www.1mind.com/ [https://www.1mind.com/] Connect with Nathan: https://founderpath.com/ [https://founderpath.com/]

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 [https://youtu.be/JQA3RX9PsHw] Connect with Ahikam: https://safebooks.ai/ [https://safebooks.ai/] Connect with Nathan: https://founderpath.com/ [https://founderpath.com/]

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 [https://www.youtube.com/watch?v=U2RAjHVdHZM] Connect with Miles: https://www.flossy.com/ [https://www.flossy.com/] Connect with Nathan: https://founderpath.com/ [https://founderpath.com/]

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 [https://youtu.be/gtFt5exyCaI] Connect with Brian: https://flipcx.com/ [https://flipcx.com/] Connect with Nathan: https://founderpath.com/ [https://founderpath.com/]

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 [https://youtu.be/2ySF3YMDcnY] Connect with Dan: https://kadence.co/ [https://kadence.co/] Connect with Nathan: https://founderpath.com/ [https://founderpath.com/]