SaaS Interviews with CEOs, Startups, Founders

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?