Clate Mask and he has been educating and inspiring entrepreneurs for over a decade. He’s recognized by the small business community as a truly visionary leader. His passion for small business success stems from his personal experience, taking Infusionsoft from a struggling startup to an 8-time Inc. 500 and Inc. 5000 winner. As CEO, he’s leading Infusionsoft on its mission to create and dominate the market of sales and marketing software for small businesses. Under Clate’s leadership, the company has landed 4 rounds of venture capital including a $55M series D led by Bain, with contributions from prior investors including Signal Peak Ventures and Goldman Sachs. He’s also named Ernst and Young Entrepreneur of the Year Finalist, a Top 100 Small Business Influencer by Small Business Trends, and one of the 100 Most Intriguing Entrepreneurs of 2013 by Goldman Sachs. Famous Five: Favorite Book? – Crossing the Chasm and The Advantage What CEO do you follow? – Marc Benioff Favorite online tool? — Thumbtack Do you get 8 hours of sleep?— Never If you could let your 20-year old self, know one thing, what would it be? – Clate wished he knew that business, not law, was the path for him AND that building a team and culture is far more fun than making money.   Time Stamped Show Notes: 01:18 – Nathan introduces Clate to the show 02:28 – When you serve small businesses, make sure you have the right target customers 02:35 – There are 27M small businesses 03:02 – “You got to get it right. You got to get the market fit” 03:20 – Infusionsoft focuses on businesses with 2-25 employees but the sweet spot is 2-10 employees 03:28 – Average customer pay per month is $250-300 03:54 – “It’s CRM, marketing automation, sales automation, e-commerce on one suite” 04:03 – Majority of Infusionsoft’s revenue is SaaS 04:10 – Infusionsoft’s $3.4B payments processed 04:36 – Infusionsoft created their own payment solution 2 years ago 05:04 – It triggers all kinds of Infusionsoft’s automation 05:50 – Infusionsoft started in 2002, as a software company 05:56 – Infusionsoft pivoted in 2007 and decided to really go for it 06:16 – “We started, like every small business, with no intention to build something big” 06:34 – Clate saw how Salesforce moved upfront quickly and that opened up the opportunity for Infusionsoft 06:43 – “Why not be the Quickbooks to sales and marketing software” 06:53 – Infusionsoft’s dark days 06:56 – In the first 3 years, every day was a fight for survival 07:43 – The second dark day for Infusionsoft was when their product market fit went off and the churn rate went up to a 8% gross monthly customer churn 08:08 – Infusionsoft had raised $17M when their churn skyrocketed 08:38 – Infusionsoft’s churn rate is usually 2-2.5% 09:15 – Infusionsoft has raised a total of $125M and about half was capital for the business 10:00 – “When you create something that’s growing, there’s always a new investor who wants to replace an old investor” 10:27 – When the round becomes “over-subscribed”, you have to take a percentage of what you’ve raised and make it available for your existing shareholders to sell some shares 11:09 – Infusionsoft currently has around 600 employees and still continues to grow 11:20 – Infusionsoft has around 135K users 11:30 – Infusionsoft just completed their 10 year adverse completion 11:56 – There are more things coming up for Infusionsoft 12:27 – Average MRR 13:19 – Clate shares why they haven’t gone public 13:58 – What happens is private money is easier to raise 14:06 – Historically, public valuation was better than private valuation, but that shifted over the years 15:00 – When the market changed in 2014, Clate had decided that it’s better to stay private as long as they could 15:30 – Infusionsoft is currently between $100M – 150M ARR 15:51 – The leverage that Clate pulled to turn their monthly churn 16:10 – Infusionsoft is serious about helping small businesses succeed 16:22 – The breakage model that results