SaaS Interviews with CEOs, Startups, Founders

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/

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/

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/

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 monthly revenue with roughly $40K in monthly profit.
What makes this business interesting is that it scaled in a legacy industry without paid acquisition or outbound. Buildern built an inbound engine around high-intent SEO, stayed profitable, and is only now adding a sales team as ACV moves closer to the range that can support quota-carrying reps.


You'll learn:
How Buildern found an underserved construction software niche.
Why Hmayak shut down a $3M dev shop to go all in on SaaS.
How the company raised just $500K and sold only 10%.
What $160K in monthly revenue looks like at a $40K profit level.
Why 95% of revenue came from SEO-driven inbound.
How Buildern chooses long-tail keywords in construction.
Why transparent competitor comparison pages rank well.
How internal SEO execution beat the need for an agency.
What changed once the company started hiring sales reps.
How pricing moved from roughly $6K ACV toward $7.5K to $8K.
What AE quotas and compensation look like at this stage.
How a profitable vertical SaaS company scales with a global team.


Hmayak came into Buildern after years in SaaS development, travel software, and running a dev shop that peaked at about $3M in annual revenue. He launched Buildern in 2021, spent the first two years without paying customers, then used industry-informed angels and product iteration to find the right shape of the product.
This episode is for founders building in old industries, operators trying to scale efficiently, and investors who care about profitable SaaS growth. It is a useful masterclass in vertical SaaS positioning, SEO-led demand generation, and disciplined capital use.


Watch this episode on YouTube: https://youtu.be/An0n18v4j8E 
Connect with Hmayak: https://buildern.com/ 
Connect with Nathan: https://founderpath.com/