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

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/

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/

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/

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/

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/

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/

暂时无法获取单集简介，直接播放听听看吧～

How do you build an AI SaaS company to $1M+ ARR with just a few dozen customers and raise a Series A at a 20x+ revenue multiple while competing against general-purpose AI tools? Tal Kirschenbaum is the Co-Founder and CEO of Ledge, an AI-native financial close platform helping finance teams automate the month-end close process. Just three years after writing the first line of code, Ledge has reached $1M+ ARR with ~24–36 customers paying roughly $3K per month, while targeting 300% year-over-year growth with a team of ~35 employees. What makes this story interesting is how narrowly the product is positioned. Instead of building a generic "AI for finance" tool, Ledge focuses on a painful operational workflow: the month-end close process for mid-market and enterprise finance teams. The pricing is not seat-based. Instead, revenue scales with operational complexity — entities, currencies, and integrations — creating a natural ACV expansion motion as customers grow. You'll learn: - Why Ledge targets finance teams with 5+ people as the ideal entry point for workflow automation. - How pricing based on business complexity (entities, currencies, channels) replaces traditional seat-based SaaS pricing. - The math behind reaching $1M+ ARR with ~24 customers paying ~$3K per month. - Why focusing on one painful workflow can create a stronger product moat than building a broad AI platform. - How "glassbox AI" explainability matters for finance and accounting teams dealing with compliance and audits. - Why selling based on workflow value — not an "AI budget" — reduces churn risk in AI SaaS. - How enterprise credibility increases ACV over time as new customers pay higher prices than early adopters. - What raising a Series A at a 20x+ revenue multiple says about early-stage AI SaaS valuations in 2026. - The internal debate founders face when trading equity dilution for faster growth. - Why some SaaS companies avoid seat-based pricing when automation actually reduces headcount needs. Before starting Ledge, Tal led M&A transactions at Meta and worked on new products at Melio, the payments company that later sold to Xero for $2.5B. He left Melio in 2022 to build Ledge, giving up seven-figure unvested equity to pursue the opportunity he saw in financial close automation. If you're building vertical SaaS, AI infrastructure for finance, or enterprise workflow software, this episode is a masterclass in product focus, pricing strategy, and early enterprise traction. It's also a rare look at how AI SaaS founders think about moats when the platform risk from large models is real. • Watch this episode on YouTube: https://youtu.be/EGWc23BI7Zw • Connect with Tal: https://ledge.co • Connect with Nathan: https://founderpath.com/

How do you turn a failed public ecommerce company into a $5M ARR enterprise SaaS platform serving ~$2M+ contracts — while rebuilding with capital efficiency after bankruptcy and avoiding the growth-at-all-costs playbook? In this episode, Nathan sits down with Jared Yaman, co-founder of Spresso and former founder of Boxed, the bulk ecommerce company that scaled to $187M in revenue before its IPO and eventual Chapter 11 restructuring. Today, Jared leads Spresso, the enterprise ecommerce software platform spun out of Boxed, now serving roughly 15 enterprise customers worldwide and growing ARR from $2.5M at spinout in 2023 to about $5M in 2025 through large ACV enterprise contracts. What makes this story interesting is the transition from low-margin ecommerce operations to high-margin enterprise SaaS. Boxed generated hundreds of millions in revenue but operated on ~4–5% contribution margins. Spresso keeps the infrastructure, data, and enterprise relationships — but monetizes them through implementation fees and modular SaaS subscriptions, fundamentally changing the economics. You'll learn: - Why scaling revenue without contribution margin destroys optionality, even at $100M+ revenue - How enterprise implementation fees subsidize onboarding costs and accelerate payback periods - The pricing structure behind $2M+ enterprise contracts in ecommerce infrastructure - Why founder-led sales and existing network relationships became the primary GTM channel post-spinout - How to reposition operational technology into a standalone SaaS category buyers understand - The debt strategy Spresso uses to keep leverage under 10% of ARR - Lessons from raising $380M in venture capital and ending with low single-digit founder ownership - How reducing deployment timelines from 4 months to 4 weeks unlocked enterprise expansion - Why enterprise SaaS growth favors fewer customers with large ACVs over broad SMB distribution - The strategic shift from retail unit economics to recurring software margins Jared previously co-founded Boxed, raising roughly $380M before taking the company public, where founder ownership diluted to about 2.6%. After Boxed filed for Chapter 11 in April 2023, he helped spin out the software platform into Spresso with debt financing support, rebuilding the business around sustainable SaaS economics instead of venture-funded retail growth. This episode is for founders navigating pivots, operators moving from services or commerce into SaaS, and investors studying capital efficiency in enterprise software. It's a masterclass in restructuring strategy, enterprise pricing, and rebuilding a company around durable margins instead of headline revenue. Watch this episode on YouTube: https://youtu.be/vslJtgAtjuY Connect with Jared: https://www.spresso.ai/ Connect with Nathan: FounderPath.com

How do you turn a niche offline sports business into $3M in contracted ARR across 200 locations, while raising $8M and keeping pricing simple on a per-unit basis? Ben Borton is the Co-Founder of PodPlay Technologies, a vertical SaaS platform powering pickleball and racquet sport venues. What started as internal software for his own ping pong spaces is now a $3M contracted ARR business serving 200 locations and roughly 2,000 courts, with ACVs ranging from $10k–$15k and an $8M Series A completed in 2025. This business is interesting because it didn't start as software. Ben built PodPlay to solve utilization and operations inside his own physical venues, where courts generated $30 per hour at 70% utilization. The SaaS product is now growing faster than the brick-and-mortar business — proving that real-world operational pain can be the most durable GTM wedge in vertical software. You'll learn: — How Ben validated the SaaS by first using it inside a venue doing $100k–$400k in annual revenue — The exact per-court pricing model and why ACVs land between $10k–$15k for larger operators — How software-only contracts at $2k–$6k expand into $10k+ hardware-inclusive deals — Why 70% court utilization at $30/hour created the margin profile to fund early product development — How founder-led sales drove growth from first external customers in 2023 to $3M contracted ARR — The GTM motion behind signing 200 locations without a traditional enterprise sales team — How viral video sharing from players became an organic acquisition channel for physical venues — Why vertical SaaS embedded in real-world workflows wins over generic booking tools — How spinning out the software into a separate entity unlocked an $8M Series A — What operators should consider before raising capital versus compounding through cash flow Ben's background spans fintech, hedge funds managing $300M AUM, and early-stage investing before launching his own venues in 2020. He opened PingPod during COVID, optimized for utilization and unit economics, and then spun out the internal software into PodPlay once external demand became clear. The capital raise was deliberate: sell 13–18%, accelerate distribution, and double down on category leadership. This episode is for founders building vertical SaaS, operators sitting on proprietary workflow data, and investors looking for software businesses born out of real revenue. If you're thinking about pricing per unit, founder-led GTM, or when to separate software from services, this is a masterclass in capital-efficient category creation. • Watch this episode on YouTube: https://www.youtube.com/watch?v=SB8bmy8LylI • Connect with Ben: https://podplay.app/ • Connect with Nathan: FounderPath.com