Got a good one for you today, I’m talking to Nathan Barry, founder of ConvertKit.

Nathan runs an impressive self-funded business for a long time now. Nathan started with info-products, books, training and apps. Finally he ended up building ConvertKit, the email marketing SaaS application, which has had a really impressive growth.

It’s always great to catch up with Nathan, because, as many of you already know his story especially from the earlier years, I could dive in in to the questions I wanted to ask him. We covered many topics that you probably haven’t heard elsewhere.

We dug into some of the tactical outbound sales strategy that he used early on in ConvertKit and how that scaled to today. Also, we talked how he was able to grow the team, and his thoughts on staying profitable and self funded, and when to invest cash into your business.

Lot’s of insightful and inspiring stuff with Nathan. Enjoy!

Episode Notes

[2:26]  Early Sales process and niching down. Tactics in building the lists to outreach. Twitter for discovering people. Exact email sequence he used to cold outreach bloggers.

• “I don’t think you can do cold outreach if don’t have a really specific market, because you are not building up the momentum. The reason you do cold outreach is to get that momentum in a specific area, so it feels like everyone is using your product.”

[13:40] What led Nathan to do cold sales email outreach every single day. Scaling the outreach process. Meeting clients in their cities.

• “Hopefully there will come a time that you desire to make this product a success will out-weight your fears of getting out of your comfort zone.”

[23:51] Self-funding. Profitability. 2-questions framework to feeling confident to invest our personal money into the business, or shutdown.

• “That gave me the confidence to looking back, if it’d failed, I’d have been able to say ‘yep, I gave my best shot and didn’t work out‘, rather than always asking ‘could it have worked?‘.”

[30:48] Keeping costs in check. Embedding frugality in the company’s culture.

• “Money was not an option to solve problems. We had to do it in a different way.”
• “I think a lot of bootstrappers use bootstrapping as an excuse for laziness.”

[37:17] How marketing looks in 2018 for ConvertKit. Why they are organizing a conference.

• “Education is a huge thing for us, teaching people how to earn a living online.”
• “We help creators earn a living.”

Links

• Nathan Barry on Twitter
• Nathan Barry’s company, ConvertKit
• Nathan’s Personal Blog
• Josh Pigford Twitter thread on  bad cold emails
• MailChimp
• Trello
• BuiltWith
• SaaStr Annual Event
• Traffic Conversion Summit in San Diego
• TradeCraft, ConvertKit’s Online Magazine
• Craft + Commerce ConverKit’s Conference

People Mentioned

• Pat Flynn
• Chris Guillebeau
• Tim Ferris
• Taylor Swift
• Mike McDerment from FreshBooks
• Seth Godin
• James Clear
• Sean McCabbe
• Casey Neistat