Rob Walling on the small steps he took to get from side hustler to indie hacking legend

Rob Walling was indie hacking before it was cool and now he’s a legend in the space. He's built multiple products, ranging from small side hustles to Drip's impressive $2M ARR and 8-figure acquisition.

These days, his ecosystem of products, which includes MicroConf and TinySeed, is making millions every year.

I caught up with him to learn from his 2+ decades of experience. Here's what he had to say.👇

How it all began

James: Where did it all begin?

Rob: Twenty years ago, I just wanted to work for myself.

I did some freelance work and ran a micro agency for a while, but I quickly realized that it was a hamster wheel. I wasn't building equity so I didn’t want to do it long term.

James: So what did you do?

Rob: After dabbling in real estate for several years and realizing I had no advantage with it, it occurred to me that I did have an advantage in software because I was a developer.

At the time, software developers were either consulting or raising venture capital. I didn’t want to do either, so I started building small income-producing websites.

There were exactly zero people that I knew doing this back in 2003.

James: Did it work?

Rob: I eventually had a minor success that was making a couple hundred dollars a month.

I realized it was a lot harder than it seemed, so a few years later, I acquired an invoicing software product that was in alpha. It had bugs, the founders had pissed off alpha users — the whole thing.

That was my first taste of making a few thousand dollars a month. And I learned a ton.

James: Then what?

Rob: Over the next few years, I launched and acquired enough small products and websites that I bought out all of my own time. I worked my last consulting hour in 2008. That was an amazing moment.

I was making $150k/yr, just living the dream. The challenge was that it was very, very hard to grow. I was trying to keep a lot of plates spinning — probably ten or twelve, and I just kept adding them.

James: Were they all similar?

Rob: No, I had a blog, four little software products, a book, a membership site, three or four info products about varying topics, and a podcast.

James: How did you juggle it all?

Rob: I tried to put them on autopilot, but they would get smacked by Google or a competitor would come around or adwords would stop working, and I didn’t have time to focus on them. So then I would either shut them down or sell them.

James: Doesn’t sound sustainable.

Rob: Yeah, I realized that running all these little products was more trouble than it was worth. I wanted to focus on one or two. And I wanted to focus on the personal brand side of things.

So I shifted my focus to writing books, doing the podcast, and building MicroConf.

James: And you sold or shut down the rest?

Rob: Yes, and I leveraged those sales into another product that I grew to $30k/mo. But I realized the platform risk would kill it so I started working on Drip. I sold that in 2016 and used it to get started on TinySeed.

James: And where’s everything at now?

Rob: The entire ecosystem generates several million dollars per year. But that’s not what I personally take home.

That's about as detailed as I am allowed to get given that I have co-founders, investors, etc.

James: What does the ecosystem consist of today?

Rob: Really, MicroConf and TinySeed are my two businesses. They are both 7 figures.

The podcast isn’t really a business, but it’s becoming one.

And there are my books too. The SaaS Playbook has sold 23,500 copies, which means just under $400k, since I launched it last year. And I self-published it.

James: Sounds like quite a journey.

Rob: I really did travel the stair-step method that I always talk about.

The stair-step method

James: Tell me about that.

Rob: I'm just not a big risk taker. I want to stay in my comfort zone. So I started small and took small steps into still-familiar territory.

So it was freelancing, then a little software product, then slightly bigger software products and info products, and then a SaaS, and so on.

James: How much bigger should each step be?

Rob: I like the next product to be 5 or 10 times larger, in terms of revenue and impact — but still within familiar territory.

James: Is that the right way for everyone?

Rob: Not everyone. Honestly, it's a little limiting and it’s one of the reasons it took me so damn long to get where I am today.

I was tentative. I wasn’t confident in my ability to execute. I had no backup and I was scared that I would wreck my life.

Someone with more confidence could get here a lot faster. But for me, this is the journey that I had to take.

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Start small, stay small (maybe)

James: This method plays into your maxim (and book) “Start small, stay small”. Should all indie hackers do this?

Rob: Well, some founders should start small and stay small. Some should not. It depends on your goals.

If you are willing to risk it all, invest 5-10 years of your life, raise a lot of money, and go high-pressure for a billion-dollar outcome because you want to be worth $100 million, then don’t start small and stay small.

But I think most founders should have a small win before they go for that outsized outcome anyway. Y'all only have so many at-bats in this life.

James: How do you start small?

Rob: You start with a small idea — a step 1 or step 2 idea — and build it to a few thousand dollars a month in a small niche.

James: Simple as that.

Rob: It’ll be easier to out-market people in a small niche. It’s way easier to get to $2k/mo than it is to get to $200k/mo.

James: True.

Rob: You’ll learn so much from the experience. You’ll gain confidence in your own abilities. You’ll gain experience with writing copy and marketing and sales and shipping and support.

And while the outcomes are unlikely to ever be $100 million, they're really, really likely to be $10,000/mo. And at that point you only own all your own time, and then you can take that big at-bat.

James: From there, why stay small?

Rob: If your small idea grows into a $100k/mo business, then ride that. You got really lucky and that's amazing. Don’t look the gift horse in the mouth.

But most of these smaller businesses in small niches plateau pretty quickly.

James: Anything that can be done about that plateau?

Rob: I used to put plateaued products on the side. Then I would go and build or buy the next one and just kind of cobble them together to build a portfolio

But if you go that route, don’t kid yourself that your portfolio will live forever. There’s a half life of products — without attention, they will slowly die.

After you’re making enough to work on the product full time, it may be worth pushing beyond the plateau.

James: How?

Rob: There's no right answer here. That's a whole strategy discussion.

Maybe you launch something. Maybe you move into an adjacent niche or add other verticals. Maybe you add more features so that you can charge more.

Good vs catastrophic businesses

James: These days, you've got a pretty interesting vantage point.

Rob: Yeah, I'm at about 195 investments with TinySeed. I think it gives me pretty unique insight.

James: What patterns have you noticed across all these businesses?

Rob: I’ve noticed that the founders are a big part of the success. And vertical software that caters to a specific niche is almost always better for bootstrappers than horizontal.

In addition, there's a third kind of software and I coined a term for it a month ago: “Orthogonal”. It’s horizontal, but it focuses on a specific role or title within a company.

James: Interesting.

Rob: When I look across all my investments, the horizontal plays tend to be in markets that are bigger with more funding. And thus, bootstrappers are at a disadvantage, unless they go vertical or orthogonal.

Vertical and orthogonal are better plays. It doesn't guarantee success, but it is a pattern that I'm noticing, and it makes it just a little easier.

James: Other than that, what makes for a good business, in your eyes?

Rob: At TinySeed, we have to narrow 600 companies down to 20 twice a year. We start by looking at the numbers.

We don't invest pre-revenue because I want to know that people will pay for it. If they will, it indicates value. And it indicates that the founders actually ship things and market them.

Revenue can tell you a lot, but you have to couple that with churn. High revenue growth with high churn tells me that the founders haven’t solved a problem that people actually want to pay for long term.

So the first round really is just metrics.

James: What next?

Rob: We have something like 30 factors that we look at. But if I were to boil the whole process down to just three factors, they would be:

1. People — like I said, founders are important.

2. Product-market fit

3. Price sensitivity of the market

James: Let’s start with people.

Rob: We evaluate whether these founders are ambitious and if they’re gonna ship. Are they tentative or executing? Do they understand the space?

James: Product-market fit?

Rob: Have they built something people really want enough to pay for it? Is their churn low?

James: Pricing sensitivity?

Rob: Who is the target and what is the price? We probably won’t fund you if you’re B2C, because we know how price sensitive consumers can be.

If your price points are low, it doesn't mean we aren't going to fund you, but we want to know whether we can raise them.

Because building a seven- or eight-figure ARR company when you're charging $20/mo is very, very difficult. And I would say that for bootstrappers, it's nearly impossible.

James: You never fund B2C?

Rob: In all of my experience and the experience of founders I've invested in and worked with, B2C SaaS is almost inevitably terrible.

The economics are terrible, the churn is ridiculous, you can't charge very much, and it's high support. So I think B2C is a catastrophic decision.

James: Strong words!

Rob: A lot of founders ask me about two-sided marketplaces too. And if you think starting a SaaS is hard, try having two customer types instead of one. It isn’t just twice as hard; it’s exponentially harder.

Do not bootstrap a two-sided marketplace unless you already have access to one side.

Rob's playbook

James: If you were starting a SaaS today, how would you do it?

Rob: I would:

1. Figure out what problem I’m solving and for whom

2. Get a landing page up

3. Start talking to potential customers

4. Look at all the marketing tactics I know and prioritize them based on the I.C.E framework

5. Start shipping stuff.

James: So you would start marketing prior to building.

Rob: Yes, start marketing immediately. You are fooling yourself if you think your product will market itself.

Get that landing page up. Start having conversations.

James: What do indie hackers need to know about marketing?

Rob: Without knowing who you're building for, you are just coding in your basement. You aren’t building a product.

And if you don’t know how to reach those people, you are wasting your time.

James: For sure.

Rob: When founders come to me today and say, “I have an idea for a product”, I say, “Don't tell me your idea; tell me what problem it solves, and for whom.” Then I ask, “Where do those people hang out and how will you reach them?”

I have a framework for prioritizing marketing tactics in The SaaS Playbook. But you need to know who you’re solving a problem for and where they hang out before you can even begin to have that conversation.

And “Twitter” is not an answer.

Skip the audience

James: Let’s talk about that. You’ve got a big audience. How important is it?

Rob: At least once a week, someone posts this very generic advice that they obviously heard from some information marketer at some point: “Build an audience, then sell stuff to that audience.”

And that’s great if you’re gonna sell information. If you’re gonna sell a book, a course, etc., then do that.

But if you’re gonna build a SaaS, ignore that advice.

James: Why?

Rob: Building a SaaS around an audience doesn’t work 99.5% of the time. There are a handful of success stories, but not many.

I didn’t have an audience for my first 10 or 12 businesses.

James: And now?

Rob: MicroConf and TinySeed are different from SaaS. These are audience-based and reputation-based businesses.

That means they’re all about producing content and building trust.

So if you’re selling books, courses, events, etc., build an audience.

And then build an ecosystem where everything feeds everything else.

James: How does that work?

Rob: My book feeds into the podcast and vice versa. They both feed into MicroConf, which feeds into TinySeed.

And the thing that ties it all together is the mission — multiplying the world's population of independent self-sustaining startups.

Don't stick around

James: Heck of a mission! Any parting words?

Rob: I had plenty of failures along the way, but I didn't let the failures drag me down.

Don’t stick around with the failures; take the learnings and use them.

James: Where can people find you?

Rob: I'm on X. You can check out MicroConf, TinySeed, or my podcast. And my latest book is The SaaS Playbook.

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