I Spent 24 Hours With A SaaS Millionaire

'Tentpole strategy': instead of marketing the core product (TaskMagic) with free info content, sell functionality via small, cheap standalone products. Step 1: build for the core customer's next problem (TaskMagic's buyers were business owners, agencies and freelancers who need sales). Step 2: keep it very simple and specific, e.g. Mail-Lead, a basic cold email outbound tool, because specific products ('cold outreach email for some sector') rank faster on SEO than a general one. Sell it to existing customers and let its own SEO attract new ones. It is its own product, not a white-label.

Make sure each side product hits a natural upgrade path to the core. In Mail-Lead, once users want to connect it to other apps they use, they click the automation button/tab and land in TaskMagic, built in seamlessly. When they hit a limit there, they start paying for TaskMagic. Users often found Mail-Lead without knowing TaskMagic existed.

Last step of the tentpole strategy: ask what the side product's users need next. Mail-Lead users need leads to email, so they built LeadQuest (leadquest.ai) for lead search. From LeadQuest, the automation tab sends users to TaskMagic (e.g. auto-send found emails via Gmail), and users who want to mass-email their leads buy Mail-Lead. Jeremy says if he started over he would make LeadQuest the tentpole; the products are not separate side hustles but serve one ecosystem.

Early on, customers didn't want to keep paying subscription pricing. TaskMagic offered a lifetime deal combined with usage-based pricing so the business could bankroll itself at the beginning. (TaskMagic later won an AppSumo award.)

Decided to explore a sale at a peak, right after making the Inc. 500 list, with a personal goal of exiting before 38. Talked to a couple of brokers, who made introductions, and listed on the Acquire.com marketplace. Bought out investors first, which drained both business and personal bank accounts; covered bills with $50K on an Amex card and $200K more in personal debt during a 6-7 month process.

In 2021, with a seven-figure no-code app builder, they stepped back to look for a bigger opportunity. Customers kept asking how to automate things, and many Zapier users were blocked because Zapier depends on APIs. They built TaskMagic to automate the 'messy' human behavior in a web browser for those users.