RVE 102: Bootstrapping a Software Startup to $10 Million
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RVE 102: Bootstrapping a Software Startup to $10 Million

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Listen to this episode in iTunes.

To celebrate 100 episodes of the RV Entrepreneur podcast, this week I kicked off a new series called “Make me feel dumb”.

The idea behind this series is to bring on guests who can challenge us in various areas of our business. These episodes are a mixture of coaching calls, interviews and me awkwardly trying to explain the parts of our business where I’ve been dropping the ball.

I selected the guests based on areas of our business where I really wanted (and needed!) someone to come in and audit progress.

The first topic we’re tackling in this series is bootstrapping a software startup. For the past year, I’ve been working to get traction with Campground Booking, an online reservation system for campgrounds. I invited my friend Nathan Barry onto the podcast to ask him questions about how he bootstrapped his startup, ConvertKit to $10 million dollars in revenue.

In addition to better understanding Nathan’s trajectory, I asked him to dive into some of the decisions we were making early on in our business to see what or how he would do things differently.

5 Things I Took Away from This Interview

Bootstrapping a software startup is hard. I had no idea actually how hard it would be. I sold software after college, but was involved very little in what it took to build that business. I didn’t feel the pain of getting it off the ground or finding product-market fit.

In this episode, Nathan hammered me with questions about my time commitment to Campground Booking, our over-all decision making and how to set proper expectations early on while getting initial customers.

Here’s what I took away from our conversation:

1. Don’t wait for the perfect product to close a deal.

You’re a startup. You will never have the functionality that they say they need. It’s just never going to happen where you’re going to walk into a sale and someone’s going to be like, you know what? This is magic.”

2. Sell around functionality.

“You’ve got to talk through how it will solve their problems. You say,”Yeah we’re missing this functionality, but tell you what, until it’s built we’ll do that part of it manually for you.” It’s your job as a salesperson to overcome those objections because they’re always going to be there.”

3. Document feedback from potential customers.

“So even to this day, after every meeting that I have,  I’ll type up all of the notes and share it with my team. I’ll say,”Okay, I can win this deal if we have this functionality.”

4. Don’t believe customers who haven’t paid you.

They aren’t vested in the product and can steer you in a million, irrelevant directions. Don’t listen to them.

5. Don’t let up.

The truth is that building a software company is so hard that if you get it to 1000 bucks a month in revenue, you deserve respect. That’s how I feel. And I think a lot of people feel that way as well.

Connect with Nathan Barry

So appreciative of Nathan being a guest on this episode. If you enjoyed this episode, shoot Nathan a tweet and let him know!

@nathanbarry on twitter

ConvertKit is Nathan’s email marketing company (and who we’ve used to send our emails for the past two years). I highly recommend checking them out!

Follow Heath:

Husband to Alyssa. Host of The RV Entrepreneur Podcast. I love RVing, that's why I talk about it so much.