Why did you decide to be an entrepreneur? I really didn’t want to work for other people. I wanted the freedom to make things.
I wanted to justify the time it takes to make something by selling what I make. Example: In high school I wrote nonfiction booklets and sold them through classified ads.
I was looking for ways to own my own time. I tried several different businesses until I finally realized I have this skill that so few people have [programming and marketing]. Why don’t I double down on that?
I didn’t know it at the time but my decision to start writing a blog was the seed for every thing else I did [like MicroConf and my podcast].
I took an unusual approach to entrepreneurship. I noticed there were all these little tools and businesses that weren’t making much money. I’d buy them and apply my tool set [SEO, AdWords, copywriting]. I had a portfolio of these little products. 6 or 8 of them. Together they generated $10,000 to $12,000 a month.
This all started by asking myself: Could I just buy one product that is kind of working, and make it work more? So I can skip all the trial and error.
I didn’t know what to do with my time once I was freed from my job. I just started pouring out more information. I blogged more, podcasted more, and started a conference.
I found a way to find neglected apps [and potential business opportunities]. In 2011, I started searching for top 100 startups of 2006, top 100 startups of 2007 etc. Then I would cold email the founder to see if they want to sell.
Why Rob wrote the book Start Small, Stay Small: I was 5 years into the blog. I had this massive list of questions people would send me about starting a company. I realized I had some knowledge to share. I could write a book answering these questions. I had imposter syndrome, but decided to try anyways. Before writing the book I put up a landing page to gauge interest. Around 600 people gave me their email. I thought I could sell 200 copies at $30 each for a total of $6,000. It took me 2 to 3 months to write. I sold 300 copies the first month. It kept selling a few hundred copies a month. So far I’ve sold 11,000 copies and made about $250,000 from it. It was self published.
Great Ben Franklin quote: Experience keeps a dear school, but fools will learn in no other, and scarce in that. What that means is it is great to learn from your own mistakes. But it is better to learn from other people’s mistakes so you don’t have to make those mistakes yourself.
The thought process to starting Drip: I wanted to know what it was like to run a 7 figure business. I wondered if there was something out there that could be a higher price point [higher than $10 a month], lower churn, and not built on someone else’s platform [Google or Twitter etc]? I built a little email capture widget. That eventually turned into a email service provider like Mailchimp.
How did you validate the idea for Drip? Before writing a line of code I asked 17 founders I knew. I described what Drip would do and the value it would provide. I asked them if they would pay $99 a month for that? 10 of them said yes.
Drip got stuck for a little bit once we got to around $8,000 in monthly revenue. Customers would cancel after a month or two because they thought it was too expensive. When this happens some founders lower the price. Instead I asked the customers [that cancelled] what features would make it worth the price? That’s how I found out about marketing automation. That’s the path we decided to go down.
You sold Drip. You don’t need to work anymore. Why start TinySeed? I wondered why there wasn’t an accelerator for people who want to bootstrap their company. An accelerator that provided enough funding to get to the point where you are sustainable.
TinySeed is the first startup accelerator designed for bootstrappers. It is a remote accelerator that lasts 1 year. Why a year? It takes a long time to grow SAAS apps.
I’m not anti VC funding. I never have been. I’m just anti everyone thinking that is the only way to start a business.
Advice for people thinking about starting a company: Know that it will be harder than you think and start small. You don’t have to stay small but you should start small.
