The Top Entrepreneurs in Money, Marketing, Business and Life

Sid Bendre and his co-founders at Oleve built a $6 million ARR mobile app empire with just 6 people, generating $500,000 monthly revenue and 10-30% profit margins from their education apps Quizzard and Unstuck. Their first TikTok video exploded to 2.3 million views overnight, converting to 10,000 users instantly, and they've since scaled to 4 million total downloads by running 6-7 A/B tests simultaneously and building AI agents that automatically find app store arbitrage opportunities. In this episode, Sid reveals their exact "milk the alpha" playbook for building million-dollar apps in any market, including their viral TikTok formula, paywall testing strategies, and how they're using AI agents to replace entire marketing teams.

Romain Torres bootstrapped ARCads.ai from zero to $6 million ARR in just 16 months with only 5 employees, achieving an extraordinary $1.2 million in revenue per employee while staying completely profitable. He launched in January 2024, hit $5,000 MRR in his first week, crossed $1 million ARR by June 2024, and recently added $1 million in new ARR in a single month between April and May 2025. His secret weapon is an arsenal of over 100 AI agents built in Gumloop that automate everything from competitor research to content creation, allowing his tiny team to serve 4,000+ customers and compete with much larger organizations. In this episode, Romain screen-shares his actual Gumloop dashboard and reveals exactly how he built AI agents that scrape competitor ads, automatically rewrite copy, and send daily Slack alerts with replication opportunities—plus his three-channel growth strategy that's driving $500,000+ in monthly recurring revenue.

Ricardo Ghekiere bootstrapped BetterPic.io from $3,000 to $270,000 monthly revenue in just 12 months, building a $3.2M revenue AI headshot empire with 13 people and zero churn using a one-time purchase model. His affiliate program converts at 12% (versus the industry standard of 0.5-1%) with just 7 top performers driving $77,000 monthly revenue, while generating $230,000 revenue per employee. In this episode, Ricardo screen-shares his actual affiliate dashboard and revenue metrics, revealing his 7-channel growth system that compounds SEO, affiliates, and free tools to capture 500 daily leads from a hidden page most competitors can't find.

Jake Mor is the founder of Superwall (superwall.com), a mobile app paywall platform that generates $3.6 million ARR with just 12 employees by powering over 100 million paywall views monthly for 3,000 customers. His company processes $25-50 million in customer revenue each month and has built over 4,000 custom paywalls while facilitating 4-5 million new user conversions monthly across their customer base. Jake reveals his exact hybrid PLG-to-enterprise strategy that starts customers at $200-300 monthly on self-serve plans then graduates them to $1,000-1,500 negotiated enterprise deals, plus his AI demand scoring system that delivers 20-30% revenue lifts overnight for apps generating $5-10 million MRR. In this episode, Jake breaks down how 2 lines of code became a $3.6 million business, his white-glove onboarding process that takes over customer paywalls for 4 weeks to prove value, and the failed experiment database that helps customers avoid costly mistakes while achieving conversion rates of 20-30%.

Alan de Souza built Reachbox.ai (Zapmail), an AI-powered cold email outreach platform offering email warmups, campaign automation, and lead enrichment. He scaled from zero revenue to $6 million ARR in just 18 months, serving 4,500 paying customers at $110 average revenue per user while growing 25% month-over-month with only 7.5% churn rate. His 27-person team generates $230,000 in revenue per employee, with 280 active affiliates driving 35% of all customers through a 20% lifetime commission program that pays out over $50,000 monthly. In this episode, Alan reveals how he added $5 million ARR in just 6 months using systematic customer feedback from 1,500+ conversations, why he still does 10 customer calls every day, and the exact affiliate strategy that turned his customers into a revenue-generating army earning lifetime commissions.

John Rush went from building 7 VC-backed startups as a CTO to creating a $3.5 million ARR empire of 20+ AI tools, with his biggest product SEO bot generating $120,000 monthly recurring revenue using just a 2-person team. He reveals his exact 30-30-30 growth formula (30% SEO, 30% cross-promotion, 30% social media) and how his listing bot makes over $50,000 per month selling one-time payments to 1,000 new customers monthly who want access to his database of 20,000+ directories. In this episode, John screen-shares his actual Stripe dashboard showing the revenue growth and breaks down how he achieves $720,000 in annual revenue per employee by building AI agents that run his entire operation on autopilot.

28-year-old French founder David Zitoun bootstrapped Submagic to $8 million ARR in just 3 years with only 13 employees, generating $615,000 revenue per employee without raising a single dollar of VC funding. He reveals how he hit $1 million ARR in exactly 90 days using the most generous affiliate program in SaaS - paying 30% lifetime commissions to 10,000+ affiliates who now drive $1.6 million of his annual revenue while processing 5-10,000 new signups daily. David breaks down his contrarian playbook including why 70% of his team has no college degrees, how he converts 2,500 new customers monthly despite 15% churn, and the exact growth tactics that crushed the US market from France.

50% Cash, 50% stock. Bridget Harris grew You Can Book Me from 0 to $5M revenue over 12 years. David is building Capacity (previously at Answers.com which sold for ~$900M). Today, Capacity acquires YouCanBookMe in a big win for bootstrappers!

Co-Founder Eric Boduch joins Latka on stage to share how they got 2,842 leads in Q2 2017. This helped them hit $15m in ARR before growing to over $200m today in Sept 2024. Will Pendo hit $300m before Dec 2025?

Coro launched in 2015 with a bottom up approach to solving sercurity issues for the SMB and midmarket. Today, they've raised $282m in funding to go big, but how much have the founders been diluted? Can they grow into their $750m valuation?

Proposify launched in 2013 and grew to $6m revenue by 2019 before things got scary. The business was burning $400k/month, product started to stall, and a layoff was needed. How did CEO Kyle Racki announce the 25 person layoff? Is the company profitable today? Are they growing again?

Joe launched Issuu back in 2006 to help magazines move digital. He grew to $50m in revenue and raised about $50m. In March 2024 he decided to exit in a nine figure deal. How'd the deal go down? Why did he go with Bending Spoons?

In 2010, she launched one of the first chrome extensions for managing email. Boomerang quickly got 10k downloads and grew revenue using a freemium model. Today, her testing framework is enabling her to drive higher free to paid conversion rates - all from the Chrome Extension Store. Can they hit $12m ARR before Dec 2024?

Retention.com hit $22m of revenue in 2024 on the back of Adam Robinson and team bootstrapping. Wanting to get into B2B, they laucnhed an IP lookup tool called RB2B which competes with Clearbit and 6Sense. How has he used Linkedin to grow? What's driving his 8% free to paid conversion rate? Can he fix churn before its too late?

Rytis Lauris bootstrapped OmniSend to $55,000,000 in revenues. His top growth driver? SEO. Learn how he made his first SEO hire, how he structured his SEO team, and how much traffic this team drives the business today. Will he hit $70m ARR before Dec this year?

Hootsuite was the social media darling of the 2017's by trouble started after a failed $750m IPO led by Goldman. Today, original founder Ryan Holmes and team have tasked new CEO Irina Novoselsky with leading the company from $200m to $400m. She says the old SaaS playbook is dead. Its working. The firm will hit $400m by Dec 2024.

Colin laucnhed the business back in 2012 and got stuck under $5m revenue until 2018. He 6x'd the business by 2022 to $30m in revenue and hit $70m in Septemer 2024. How did he do it? Hear the 9 mistakes he made that he think you should fight to avoid.

VoxPopMe has hit $6m in revenue. Wanting to avoid dilution, CEO Andy and the board rasied $750k from Founderpath. At the same time, Founderpath worked with the board to establish a new ESOP pool for management resutling in 10%+ more equity for leaders.

Tim founded SaaS Group in 2018 using his own money from Eyeo exit to acquire Deploybot. SaaS Group is structured as an LLC and funded all deals with equity until 2020 when they began using debt. In 2024, they sold about 5% of the SaaS Group LLC for $25m implying a value of $500m. They've purchased 20 companies over the last 5 years. Their companies do $60m in combined revenue today and employ 300 people. They typically pay 2-4x multiples. DashThis, Usersnap, and Rewardful are some of their larger companies. Can they acquire $60m more in ARR over the next 12 months?

How ActiveCampaign hit $100m ARR on way to $300m

Alessandro Chesser was one of the leading sales executives at Carta for 7 years. They always talked about helping Founders set up Trusts to preserve wealth - but it never launched. In February of 2022 he left to launch Dynasty and make the Trust process easier for Founders. Why South Dakota? Revocable or Irrevocable? 0% tax or 40% tax? We talk about it all live. 

Tyler Denk launched Beehiiv after missing out on the ""Founder Money"" the MorningBrew team made when they exited. Today, his tool helps newsletter creators launch, grow, and monetize. The firm did $1.5m in revenue last month split between SaaS, ad revenue, and kickbacks on cross promoting newsletters. Can they hit $25m ARR this year?

She bootstrapped to $12m in revenue in under 18 months. Rebecca Shostak launched FloDesk.com in 2017 as an email marketing tool focused on beautiful design for solopreneurs. As of May 2024, 80,000 customers pay $28/mo on average and the firm just launched their second product: Sales funnels. She's done this all with a team of just 50 people - $540k in revenue per employee. Will she break $35m in ARR this year and remain bootstrapped?

Inside Beamer acquiring UserFlow and creating a $10,000,000 revenue machine. Userflow had no reason to sell with 50% EBITDA margins, 650 customers and completely bootstrapped. How did Beamer, using Camber fund money, get the deal done?

Sam Jacobs launched Pavilion in 2019 to help sales reps learn. Today, he does $11m in annual revenues and has expanded to CEO's, CMO's and other leadership groups. Can they hit $15m in revenue before Dec 2024?

Owner.com is a $20m ARR SaaS for restaurants that had F90 day churn of 30% before Kyle Norton joined as CRO. He fired 4 AE's, narrowed the ICP focus, and got burn multiple down from 1.2x to 0.8x as they hit $6m in ARR. Today they do $20m. Can they break $25m before Dec 2024?

The idea that AI can save you cost and help you reach profitability might be a good one. Chili Piper hit $40m in revenue and profitability as Alina built AI into more parts of the org. Here's how she did it across customers, ecosystem, and employees.

Savneet Singh was recruited to take over PAR as CEO in 2019. Since then, he's doubled revenues to $400,000,000, changed the culture, and rapidly expanded the product suite. Why is the market only valuing him at $1.5 billion? Will they hit $500,000,000 before Dec 2024?

Since StackOverflow was acquired by Prosus in June 2021 for $1.8b, most don't realize the company does over $125m in revenues today. 65% of that revenue comes from recurring revenue SaaS products where customers pay $289,000 per year on average. Will they hit $150m in revenue before Dec 2024?