SaaS Interviews with CEOs, Startups, Founders

Nathan Latka
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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.

  1. 1 DAY AGO

    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

  2. 29 APR

    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

  3. 22 APR

    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

  4. 15 APR

    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

  5. 8 APR

    How Buildern Reached $2M Revenue With 300 Customers | Hmayak Tigranyan

    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/

    18 min

  6. 1 APR

    How Allo Reached $10M Revenue With 5,000 Customers

    How do you grow an AI phone system to 5,000 customers and roughly $3M ARR in under two years while still aiming for $10M in revenue this year? Jeremy Goillot is the founder and CEO of The Mobile First Company, which launched Allo as its first product. Allo is an AI phone system and dialer for small businesses, now serving around 5,000 customers with average revenue above $160 per month and a goal of reaching $10M in revenue in 2026. This business is interesting because Jeremy did not stop at a self-serve PLG motion. He started there, saw the churn and activation issues, then layered in demos, lead routing, CRM-based qualification, and expansion to raise ACV and improve retention. The result is a high-volume SMB SaaS business built on strong distribution, fast onboarding, and clear activation metrics. You'll learn: Why Jeremy moved from pure PLG to a sales-assisted motion. How Allo increased average revenue from $18 to over $160 per month. The exact activation metric that predicts churn. How the team uses demo routing based on CRM and team size. Why retargeting was one of the cheapest acquisition channels. How Allo won SEO with long-form content and original screenshots. The keyword prioritization system behind their content strategy. Why 50% of new revenue now comes from expansion. How the team thinks about CAC quality instead of lowest CAC. Why Jeremy raised early without waiting for a co-founder. How he kept about 50% ownership after raising around $20M. What it takes to sell into SMBs at high volume with only 17 people. Jeremy previously led growth at Spendesk before starting The Mobile First Company. He launched the company as a solo founder, raised a $5M pre-seed on his own, then built the team around him while keeping significant ownership. His long-term goal is not just one product, but a broader suite of vertical SaaS tools built under separate brands. If you care about SMB SaaS, PLG versus sales-assisted growth, SEO-led distribution, or building a multi-product software company, this episode is a masterclass for SaaS builders. Watch this episode on YouTube: https://youtu.be/PUZMvjyS3xw  Connect with Jeremy: https://www.withallo.com/  Connect with Nathan: https://founderpath.com/

    23 min

  7. 25 MAR

    How TitanX Hit $9.7M ARR After Buying IP for $200K

    How do you turn $200K into a $9.7M ARR SaaS company with a $100M valuation by buying IP instead of building from scratch? Joey Gilkey is the founder of TitanX, a sales intelligence platform generating $9.7M ARR after launching in 2024. The company serves enterprise sales teams with contracts ranging from $24K to $250K annually, with its largest deals exceeding seven figures. What makes TitanX interesting is its approach to building a moat. Instead of competing as another data provider, the company sits between data sources and execution layers, using proprietary signals and AI to improve outbound performance. The business scales through high ACV sales, expansion revenue, and strategic acquisitions. You'll learn: How Joey turned a $200K IP purchase into a $100M company Why buying IP can be faster than building SaaS products How TitanX structures pricing from $24K to $250K ACV The role of proprietary data in building defensibility How inbound, outbound, and referrals drive pipeline Why expansion revenue is core to growth strategy How acquisitions accelerate ARR growth The credit-based pricing model and consumption dynamics How TitanX uses AI to improve outbound performance The logic behind raising $27M and taking secondary cash Joey started in enterprise sales before launching multiple businesses and eventually betting his entire net worth on TitanX. After acquiring the IP in 2023, he shut down a profitable services business to focus fully on SaaS, scaling from zero to $9.7M ARR in under two years. This episode is for SaaS founders thinking about capital allocation, high-ACV sales, and building defensible data products. It's a practical breakdown of how to scale quickly using acquisition, pricing, and distribution strategy. Watch this episode on YouTube: https://youtu.be/mxiCodnXo6U?si=zebVllHlOY7UlVqO  Connect with Joey: https://titanx.io/  Connect with Nathan: https://founderpath.com/

    16 min

  8. 18 MAR

    How TeamSupport Reached $10M–$25M ARR With 1,000 Customers | Grant Stanis

    How do you grow a customer support SaaS to over 1,000 customers and $10M–$25M in ARR in one of the most crowded software categories, without trying to outspend the giants on marketing? In this episode, Nathan sits down with Grant Stanis, CEO of TeamSupport. The company provides B2B customer support software used by more than 1,000 companies and generates between $10M and $25M in annual recurring revenue. Most customers start around $10,000 per year, but the best accounts expand significantly over time, including enterprise customers paying more than $1M annually. Customer support software is a brutally competitive market with players like Zendesk and Freshdesk dominating search and advertising. Instead of fighting that battle, TeamSupport focused on referrals, community, and expansion revenue. The core idea is simple: turn support conversations into signals that drive retention, product feedback, and upsells. You'll learn: How TeamSupport grew to $10M–$25M ARR with over 1,000 customers. Why most customers start around $10K ACV and expand to $20K–$30K later. How one enterprise account grew into a $1M+ annual contract. Why they price the product per seat at $79–$99 per user. How expansion revenue became a core growth driver. Why the company relies heavily on referrals instead of SEO. How partnerships and webinars generate qualified pipeline. What it's like to lose a top 10 customer and report it to the board. How private equity ownership changes the way CEOs run SaaS companies. What kind of acquisition offer would realistically trigger a sale. Grant joined TeamSupport as CEO in 2024 after leading growth at several private equity-backed software companies. The business was founded in 2008 and later acquired by Level Equity in 2018. Today the focus is simple: grow profitably, expand existing customers, and build a durable SaaS business without relying on massive marketing budgets. If you run a SaaS company selling to support teams, customer success leaders, or mid-market software companies, this episode offers a practical look at how to grow in a crowded category. Connect with Grant: https://www.teamsupport.com/  Connect with Nathan: https://founderpath.com/

    16 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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