How Landon Bennett deftly operates 4 startups at once

Landon Bennett started out in sales before he launched and operated multiple businesses.

That skillset has been invaluable as he grew up to four businesses simultaneously— soon to be five.

He recently sold his Intercom-focused SasS, Userfeed, in a 6-figure deal and is in the midst of launching another.

I spoke with Bennett about his multiple business journey, what he’s learned, and his advice for founders.

What did you do before you started your first company?

I was both a sales rep and sales leader for another SaaS company called Rigor, which sold to Splunk last year.

Why’d you decide to become an entrepreneur?

I love creating and attempting to do things that have a high likelihood of failure. In other words, I enjoy doing hard things. Nothing is more satisfying when you achieve some success. As a kid, I always got energy from working toward things that most people thought were out of reach for me.

If you aim big and work towards it, you won’t always achieve that specific goal, but if you miss by a bit, you’re still achieving great things.

How many businesses have you founded?

Legally, three. But there are a bunch of assets under those legal entities. In total, my business partner, Kyle Conarro and I have started seven business assets, which you can see here.

We’ve made millions on those assets in the past ~5 years, but the bulk of the revenue has come from a few. I also have a business with my wife where we do some consulting and angel investing, T&L Bennett.

How many have you operated simultaneously?

Four (soon to be five). Under our parent company, Zero Mile, we’re currently we’re running two SaaS products — Ad Reform and Hillchart, one SaaS is close to launching (Docs Fresh), one podcast, Made with Grit and one recruitment business, Hire with Grit.

How do you approach your time?

Documentation is key. Notion is our central hub for documentation and communication. I typically give 80% of my time to one business at any given time. Usually, this is when we’re getting the business off the ground, then we try to put systems and/or people in place to handle the bulk of the workload.

We’ve hired a number of folks through our Filipino hiring firm, Hire with Grit, to run different aspects of the businesses.

What mistakes have made when running multiple firms?

We’ve often spent too much time on one thing when it was clearly not working.

What’d you learn from that?

We’re learning to become better at figuring out when it's time to accelerate and when it's time to decelerate or move our time to something else. Sometimes moving to something else, gives you the space to think, and you can come back to that other business with fresh energy and perspective.

Any advice for founders?

When starting something, try to do as little as possible product-wise to get a feel for demand and feedback. Use no-code tools. Do some things manually to better understand the process/use case and gaps that can be solved through tech. Get paid to learn.

Once you’ve proven demand and have figured out what needs to be built, then start investing more on the product side. Spending a lot of time and money building a product in a vacuum usually leads to lost time and money. With every new venture, we spend less time on the product upfront, yet our revenue grows faster. Imagine that!

Common pitfalls when operating multiple businesses

I don’t know a lot of people that run multiple businesses, but those that do often build a bunch of things at once and they all end up spitting out a small amount of revenue. This is unsustainable financially and will likely lead to burnout. Plus, you’re not learning certain things you’d only learn at certain stepping stones of a growing business.

How’d you avoid these pitfalls?

I’d recommend taking more of a stairstep approach. Rob Walling sort of coined this term, and a number of other successful entrepreneurs have followed it — ie. Nathan Berry at Convertkit. Build one thing. Make it successful. Build systems and hire people to operate them so that it can function and grow on its own.

Once you’ve got that machine rolling, decide if it makes sense to start something else. If so, you’ve got the time to work on it now, padding financially, and the learnings from that journey. Get some base hits, then go for the home run.

Any advice for founders hoping to operate multiple businesses?

You probably shouldn’t do it. There are a number of good arguments that it’s more productive to focus time, effort, and money on one thing. For us, we get energy from the zero to one phase, and working on different things helps us avoid burnout on one thing and gives us a bit of risk diversification.

It also lets us experiment as we continue to get better at this craft of entrepreneurship. We don’t think we’ve hit our home run yet — I believe there’s one in there — so we think more at-bats will give us better odds.