SaaS Interviews with CEOs, Startups, Founders

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/

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An engineer from a young age, previously CTO/R&D manager in a number of Israeli startups, ex-Googler turned entrepreneur and CEO, changing the US education financing. Running a successful all-remote company now for 5 years, and a strong believer in remote as a way of life.

Massimo Chieruzzi, CEO of AdEspresso. His company, founded in 2013, is now so profitable that he says they don't need fundraising! Massimo sees only growth for AdEspresso in the future as Facebook ads continue to evolve and improve.   Famous Five:   Favorite Book? – Predictably Irrational What CEO do you follow? — Rand Fishkin Favorite online tool? — HubSpot Do you get 8 hours of sleep?— No If you could let your 20 year old self know one thing, what would it be? — Don't start a startup. Get some experience for a corporate business first.   Time Stamped Show Notes: 01:05 – Nathan introduces Massimo 01:30 – AdEspresso was first on The Top on Episode 70 01:50 – Focus on growing and reducing churn 02:25 – Revenue is about $400k/month 02:38 – 2015 total revenue was $3M 02:50 – Fundraising has reached $1.8 Million 03:30 – "We have been profitable this last year, so we don't need the money." 04:00 – More than 4000 customers 04:45 – Learn about AdEspresso at Adespresso.com 05:00 – Churn is 7% and is decreasing 06:00 – How long their customers stay 07:10 – 35 people on their team 07:20 – Monthly expenses are around $280k 07:45 – They are growing by at least 15% every month 08:00 – How the company is sustainable 08:30 – Customer acquisition is less than $10 08:45 – Paid acquisition is only content promotion 09:20 – They were founded in 2013 09:30 – What would Massimo sell his company for? 10:20 – @MassimoCw on Twitter or [email protected] 12:10 – The Famous Five   3 Key Points: Allow yourself to gain knowledge from different experiences. Find ways to lower your acquisition costs. Get into an industry that has a long life ahead of it.   Resources Mentioned: Host Gator – The site Nathan uses to buy his domain names and hosting for cheapest price possible. Freshbooks - The site Nathan uses to manage his invoices and accounts. Leadpages  – The drag and drop tool Nathan uses to quickly create his webinar landing pages which convert at 35%+ Audible – Nathan uses Audible when he's driving from Austin to San Antonio (1.5 hour drive) to listen to audio books. HubSpot – Massimo's favorite online tool Show Notes provided by Mallard Creatives

Amit Kothari. He spent ten years in London dealing with some of the largest companies and organizations in the world and helping them with collaboration technology. After seeing a lot of failures in that industry, he realized he needed a very structured process with unstructured, human conversations to make his business succeed. Famous 5: Favorite Book? – The Innovator's Dilemma What CEO do you follow? — Jack Welch and Warren Buffett Favorite online tool? — DropBox, Xero Do you get 8 hours of sleep?—Yes If you could let your 20 year old self know one thing, what would it be? — "Never confuse movement with action." –Hemingway Time Stamped Show Notes: 01:10 – Nathan introduces Amit 01:45 – Tallyfy 02:05 – The company's program helps remove routine processes throughout the day 02:30 – They started in Chili with a grant in 2014 03:00 – Then they got a grant from the US 03:30 – First year had no revenue 03:45 – $300k in 2015, with $600k total 04:15 – Paying customers 04:50 -- $39/month is the average that customers pay 05:15 – Monthly revenue 06:00 – They have several different services and processes 06:35 – Pure MRR in April -- $4000 07:10 -- Professional services is a huge chunk of revenue 08:20 – Starting out with professional services brings in a lot of revenue 08:50 – Team size is 5, with a few freelancers 09:05 – Total capital $500000 10:10 – Amit and his wife are cofounders 10:25 – They have a rule to stop talking about work after 6 pm 11:00 – They believe in their business 11:45 -- tallyfy.com and @tallyfy on Twitter 12:00 – Consistency is the secret to a growing company's success 14:20 – The Famous Five 3 Key Points: Start a business that you believe in. Look for grants and funding opportunities. If you want to scale your business, you have to put effort into consistency. Resources Mentioned: Host Gator – The site Nathan uses to buy his domain names and hosting for cheapest price possible. Freshbooks - The site Nathan uses to manage his invoices and accounts. Leadpages – The drag and drop tool Nathan uses to quickly create his webinar landing pages which convert at 35%+ Audible – Nathan uses Audible when he's driving from Austin to San Antonio (1.5 hour drive) to listen to audio books. The Innovator's Dilemma – Amit's favorite business book DropBox – One of Amit's favorite online tools, that allows businesses to share files online Xero – Online accounting tool Show Notes provided by Mallard Creatives