SaaS Interviews with CEOs, Startups, Founders

He Raised $3m at a $25m valuation, is that overpriced or just right?

The Micro PE Playbook: They Bought 20 SaaS Companies, $60m ARR, 300 people

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 large...

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

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

The Revocable Living Trust Cheat Code for SaaS Founders (Save millions on taxeS)

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.

The next Mailchimp? Email SaaS Hit $15m Revenue Last Month

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?

Genius Affiliate Strategy Helps Bootstrapper Hit $27,000,000 Revenue

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?

The Inside Story of Beamer Acquiring Userflow to hit $10,000,000 in ARR

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?

How Pavilion Hit $10m in Revenue While Balancing Investor and Customer Demands with CEO Sam Jacobs

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?

$5m in ARR? Your CRO Should Be Focused on These 3 Things

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?

How Chili Piper Used AI to Hit $40m Revenue, Turn Profitable with Co-Founder Alina Vandenberghe

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.

The Secret Virtual Assistant Marketplace SaaS CEO's Spent $25m on in 2023

39 Year Old Public SaaS CEO Doubles Revenue to $400m Over the Last 24 Months - His Genius M&A Playbook

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?

How Stack Overflow Secretly Made $65,000,000 on its SaaS Last Year

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?

aHref's Does $1m in Revenue Per Employee, Bootstrapped, Using these 5 Content Strategies you should copy

aHref's generates $900,000 in revenue per employee (100 FTE's, $100m+ in ARR). They ignore Google Analytics, conversion rates, and didn't hire their first sales rep until $90m in ARR. They're bootstrapped. How do they use content to generate millions of website hits per month? Copy these 5 tactics.

CPO Does $90m in Revenue, Reveals M4 Test He Ran To Increase NRR at Month 18

Clate Mask launched Keap (formerly Infusionsoft) back in 2010 and quickly scaled to $100,000,000 in revenues in 7 years (2017). After that, the company flatlined due to competition and diluted priority. Today, CPO Ammon Curtis is helping turn things around. Learn the M4 test he ran on 705 customers to measure DIY, DFY, DWY onboarding and how this impacted long term retention and LTV. Can they break $110m in revenue before Dec 2024?

How I Used 1 Linkedin Post to Generate $1,000,000 in Pipeline and Closed $250,000 in new ARR

Adam Baker is a 3 time founder currently building DealPad. The firm did $3,700,000 in sales last year without outside funding. Can they hit $7m in ARR before Dec 2024?

$6m ARR CEO Shares When to Hire First AE, CSM, and VP

How This CEO Used Webinars - 45% show up rate - to Hit $8m in Revenue

How This SaaS Product Studio Built 3 Tools and Did $16m in Revenue Last Year

Founder Does $18m in 2023 Revenue Following 9 Strange SaaS Playbooks

Gilles Domartini bootstrapped Cleeng to $18m in revenues by focusing on 9 tactics many ignore. His 5 part pricing strategy is new. His organizational efficiency is not-common. Customers use his tool to process 48 million transactions per day adding up to $500m in annual gross billings across 35m user accounts. Will he hit $25m revenue before December 2024?

Lemlist Product Genius Shares Strategy, $23,000,000 in Sales (ARR), No Outside Funding

Lemlist has bootstrapped to $23m in ARR using a combination of Product Virality, Acquisitions, and Courses. Chief Product Officer Kévin Moenne-Loccoz tells us how they stacked growth tactics to avoid raising outside capital while still growing revenue fast. Will they hit $30m by December 2024?

$50m Bootstrapped CEO Shares His First SEO Hire, Growth Tactics and Playbook

Rytis Lauris bootstrapped OmniSend to $50,000,000 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?

Is Forecasting a Waste? CFO with $123m in Revenue Tells All

mFiles has grown from $10m revenues in 2015 to more than $123m today. CFO Justin Kim has been there for the full ride. Is forecasting a waste? How should a CFO setup a plan B? How should scenario analysis actually work?

This $100m ARR Company Is Making a Major Change to their Q3 2024 Marketing Strategy

Typeform CEO Kim Lecha is in a war with Jotform, Surveymonkey, and other form providers. His 2024 top priority is a brand new marketing approach. Will it work? Will Typeform break $180m in ARR before Dec 2024?

How to Sell your Company for $60m (from a Founder who did it)

Crossbeam CEO Bob Moore invented the term Ecosystem Led Growth. He sold his first company for $60m before taking those lessons and launching CrossBeam. Will he hit $50m in ARR before Dec 2024?

Coro Announces $100m Live on the Show, Their Partnership Playbook

Coro CEO Drew Liwer shares breaking news. He credits their revenue growth to a channel first strategy. Listen to get his playbook. Will they hit $150m in ARR before Dec 2024?

How to 3x your revenue with 3 simple pricing changes

Cledara Co-Founder Brad Leeuwen wanted to grow faster. He was nervous to change pricing. Once he did, the results shocked even him. Will they break $30m in ARR this year?

Want $100m in revenue? Copy these lessons from ZenBusiness CEO Ross Buhrdorf

How did they get Mark Cuban to invest early on? What pricing changes did they make to grow from $40m to $80m in ARR? How did Ross acquire 4+ companies? Will they break $150m in ARR by Dec 2024?

13 Lessons I Learned Bootstrapping to $20m in Revenues

TimeDoctor CEO Liam Martin has used his community to bootstrap his SaaS to $20m. He'll show you how he grew 202% in 2020 and continues to grow profitably. Can they hit $25m by Dec 2024?

How I hit $15m ARR using 4 new growth playbooks

Metadata CEO Gil Allouche almost killed his company in April 2020 when he only had $500k cash left in the bank and less than 2 months of runway. He used 4 growth tactics to turn things around, hitting $15m in ARR last week. Can he break $20m before Dec 2024?