Hey!

Heath here, writing to you on a rainy day in Portugal.

Today's email is really long but full of painful experiences turned into business lessons. This is an email I've wanted to write for at least a year.

It's also probably the longest email I've ever written.

So if you're not into reading my novel, you can check out our latest YouTube video instead:

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In today's email, I share everything I would do differently if (and when) I start another company.

If you are unfamiliar or new to our email list, I was the co-founder of a company called Campground Booking. Along with my partner, I bootstrapped it for four years, then raised $750K of venture funding in 2020 before selling it to Camping World in 2021 in a multi-seven-figure deal.

Along the way, I made a bunch of mistakes.

I don't want you (or me) to make those in your business, so I shared 9 of them below.

If you read through this email and found it helpful, I'd love to hear from you. I probably owe you a drink if you make it to the bottom of this email!

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It’s been a little more than a year since I exited my role at Campground Booking.

It’s taken some time for me to pause after startup life and catch my breath.

For a while, I haven’t wanted to work at all. Eli and Ellie are in their early and "golden" years and it's been so magical with them.

We've traveled a LOT. In the past year, we've explored Japan, New Zealand, Portugal, France, Mexico, and a bunch of other countries.

We’ve traveled and made amazing memories. I will always cherish this time.

However, after some rest time, I'm starting to feel the entrepreneur itch again.

Instead of just jumping into the next thing, I wanted to take some time to write down what I learned from my last go-around the block.

Some of these lessons pertain to relationships with cofounders or customers and some are more broad. There’s no order to them, but I wanted to write them down so I don’t forget them.

I wanted to share them with you in case they could be helpful as you’re thinking about your current or next business. But I think I mostly wanted to write them down for me, so I don't forget these big lessons before I start something new.

10 Things I'd Do Differently in My Next Startup

1. I wouldn't settle when it came to a co-founder.

My dad always told me that who I decided to marry was one of the most important, if not THE most important, decisions in my life.

Alyssa and I are coming up on ten years of being married and I can't thank my dad enough for this wisdom.

Alyssa and I have traveled the world, written books, started companies, and are now tackling parenthood together.

There have been days when I’ve curled up in a ball and cried and days where she has. We lean on each other in so many ways and also call each other out when that needs to happen (I’ve found I need this more than her).

Business isn’t much different than marriage.

When you’re building a startup, your co-founder is everything.

You talk every day. You rely on each other for important decisions. You need to have their full trust and vice versa.

It's more than just a professional relationship. They need to be someone you're comfortable spending an exorbitant amount of time with.

If you’re a combination of the five people you spend your time around, your co-founder will closely be your number one or two. If this person is a positive influence, great. If they aren’t, it will drag you down.

I made the mistake of jumping into a co-founder relationship shortly after meeting someone. A year into our company we had a messy exit and almost didn't survive.

If I could go back and do it over again, I wouldn't have rushed into this. I would have built a foundation first, just like when Alyssa and I started dating.

The odds are that your company won’t be a success (according to every statistic known to entrepreneurs), so take this into consideration. If your business fails, will the time you spent with this person be worth it?

To explain it in another way I’ll tell a quick story.

A few years ago some of my buddies and I took a rafting trip. It was early summer and it was my first time airing up the kayaks for the season. Before leaving I made the mistake of not checking for any holes. I also made the mistake of telling a friend he was welcome to use my extra kayak.

My nice gesture turned out to be an unintentionally cruel one.

For FIVE hours we had to pull over while both of our kayaks leaked air.

Because we weren’t prepared at all, we had no patches to salvage the holes (nor did we have an air pump). We were blowing up the raft with our mouths. At one point we took the wrapper off the sunscreen and stuck it onto the hole. This lasted ten minutes before it went limp and fell off.

The day got really hot and we didn’t have enough water to drink. We took turns on the failing kayaks to alleviate the pain, eventually leaving one of them behind as it completely deflated.

Hours later and dehydrated, our friend Lee almost collapsed out of heat exhaustion. Somehow, we all made it out of the water unscathed (though I felt like a complete ass for my mistake).

Years later, we now laugh at the incident.

More than laugh, we constantly reach out to each other and say “Remember the Buffalo (River)!” It’s a great story that we can all put in our pockets. It’s a type of pain that we endured as a group and one that we can look back on with fondness.

In a way, a startup journey is very similar.

It's like floating down a river on a hot Alabama day in a kayak that is constantly deflating. It’s going to exhaust you and push you to your limits.

Who do you want to surround you in the water during this chaotic mess?

Even though our day on the river was a complete disaster, I wouldn’t trade the memory for anything (Lee might, he’s still a bit sour I think). I made great memories with some of my closest friends.

The odds are that your idea or business won’t flourish. Most startups fail. Even if your startup doesn’t achieve its goals, will your time building it be worth it? Will it be a great story? If you’re building alongside people you love, then I believe it will be.

Choose your co-founders wisely. Find people you’re willing to traverse a very hard journey with. Recognize the best times will likely come as part of the messy journey and not the successful exit. The journey is all you have. Make sure it’s a good one.

2. I would focus on nonobvious startup ideas.

When I pitched people on Campground Booking, everyone agreed it was a great idea. An easier way to book campsites? Yes, sign me up.

The problem wasn't that it was a bad idea. It’s that it was too obvious.

Too obvious means competition is more prevalent. When I started Campground Booking, we had dozens of other competitors who were relatively indistinguishable from us.

On many occasions, we’d do a demo and the customer would tell us we were their sixth demo. At face value, we looked the same.

This invites a whole other conversation around how to stand out and build a better and different product than the competition, but that’s not what I’m talking about here.

If everyone thinks your idea is great, it's probably going to be easily funded and built by a bunch of other people.

Find less obvious ideas.

When I started The RV Entrepreneur podcast, people literally laughed at me. How many people are interested in running a business from their RV?

This was back in late 2015, long before the COVID boom of RV and van life.

However, I had a unique insight.

I had traveled to all 50 states the year before and actually met people on the road. I knew there was an emerging group of entrepreneurial people bucking the status quo. I had conversations with them around campfires and online. It was still a leap of faith, but I had a feeling there were more people like me than others realized.

As it turns out, I was right.

Shortly after launching the podcast, it hit the New & Noteworthy in iTunes. Nine months in, we hosted our first in-person conference with 125 people who came from all over to gather.

At the time, it was a very non-obvious business.

So what if the addressable market wasn’t huge? We were also the only shop in town. If you wanted to connect and build relationships with other people who ran a business from their RV, you came to the RV Entrepreneur Summit.

I don’t say this to brag, but to illustrate a point.

Just because people believe in your idea, doesn’t mean it’s good.

(This also works in reverse. If few people see what you see, it doesn’t mean your idea will work.)

So many famous startups had origin stories of VC’s and investors who passed on them. Non-obvious startups might have a higher chance of going bust, but they also have a higher chance of putting you in a league all on your own. Obvious solutions might get you more pats on the back, but they can lead you down a road that’s competitive and riddled with trying to be 5% better.

Nobody builds a great business being 5% better.

3. Find a boulder you can roll down a hill (aka a product people desperately want).

I heard Derek Sivers say this at a conference once and it always stuck with me.

Derek is the founder of CD Baby which he sold for $28M. Before CD Baby, he started a lot of different projects. None of them worked. With each one, he said it felt like pushing a boulder up a hill. With CD Baby, it finally felt like pushing a boulder down a hill.

He wasn’t trying to force something to work that wasn’t. He was just trying to keep it from rolling out of control.

This is a great illustration for finding a real customer pain point.

When you hit on something visceral, you don’t have to convince them. You don’t have to use tactics or sales strategies. You just tell them what you’re offering and it’s a heck yes.

I never quite experienced this with Campground Booking. At times we’d have customers eager to sign up or have them tell us how excited they were about the product, but it was short-lived (though enough for us to feel momentum and validation).

The boulder down a hill sensation more accurately describes my experience with The RV Entrepreneur podcast and Summit than it does my experience with our startup. With the conference, we would sell out tickets within the hour (even when we moved the location to rural Alabama). This was a product people couldn’t wait to get their hands on.

In my next startup, I would rather close up and walk away than spin my wheels on something that feels like pushing a boulder up a hill. This isn’t to say I won’t market the product or push past pain points, but there needs to be slap-you-in-the-face evidence from the market that you've hit on something real. Otherwise, it’s not worth the time.

4. Raise money sooner.

I was proud to bootstrap my business but I did it way too long.

Four years was too long without a real paycheck for me and my co-founder. If both of us hadn’t picked up side gigs along the way we would have burned out and quit. It created way too much stress on us, our wives, and the business as a whole.

Once we had clear evidence of a product that was scaleable and a market for it, we should have raised money to build a better product and reach more customers.

5. Have conviction in the vision (aka don’t give into fear).

I had a vision for our business that I believed would work. But I didn’t have enough belief in it to raise money, scale up the team, and execute.

Instead, I floundered and went back and forth in our direction.

At that same time, our competition executed our vision. They raised money, hired 40 people, and built a way better product than us.

If I’d had more conviction, we could have pushed forward faster and maybe won the market. Instead, I wasted too much time second-guessing myself.

Looking forward, I will focus on making a decision and living with the results, right or wrong. It’s better to move forward with conviction in a direction and then course correct versus not moving at all.

6. Don’t skimp on sales and marketing.

A pivotal moment in our business happened in March of 2020.

While COVID ramped up, I hired a close friend and entrepreneur named Garrett to help me grow Campground Booking. Garrett had spent the last few years growing sales teams and was convinced that with some work we could grow our sales teams and in turn, our business.

I wasn’t a big fan of direct sales or cold calling, but that was stupid of me. Once Garrett came on board, we saw real results.

He brought on three account executives who hit the ground running. Our product was robust at this point. We had testimonials and reviews from customers, so our sales team had an actual product to sell and it worked.

If it wasn’t for the growth we experienced from these sales efforts, we wouldn't have successfully raised our seed round or been acquired.

Because direct sales was not my forte, I waited too long to implement a strategy.

If the skills don’t exist on the team, find the person who can help. Instead of complaining that growth is stagnant or you don’t know what to do, find help.

7. Take customer feedback with a grain of salt.

In our earliest designs for a campground reservation system, we added something called yield management. This is something hotels have been doing for many years. Simply put, when occupancy goes up, so does the rate per night.

We felt that bringing this to the campground industry would be a major win.

However, in talking with early customers, they could not care less. These campgrounds were using pen and paper to take reservations, they could barely wrap their minds around allowing people to select their own campsite online, not to mention yield management.

We put yield management on the back burner and focused on the basics. We carved out a niche in helping parks go from zero to one. We’d take them from manual processes to online bookings and save them hundreds of hours each year. It was a good value proposition.

The problem came later as we tried to focus on more savvy operators. As the camping industry matured and got more attention, newer and more savvy investors started buying up properties.

When we spoke with them, they immediately gravitated toward advanced features like yield management, email marketing, and grid optimization. These were areas we had not focused on because we’d been so keen to satisfy the less technical customers.

While there’s nothing wrong with picking a market focus, we did it semi-unintentionally. Had we instead focused on where the market was going versus where it was at, it would have eventually caught up with us.

Instead, we took a small step backward to help the parks which eventually sold to younger owners anyway.

I think my lesson here is to trust your vision for a product and to take customer feedback with a grain of salt. Be okay with turning away customers who aren’t a great fit. Look at where things are going and not where they are.

8. Do less, but better.

At one point, we were a bootstrapped B2B SaaS biz with three very different products. They all sort of worked together, but kind of didn’t.

One of them was a trip planner tool we built in order to lock in a major sales partnership. At the moment it sounded good. We get some upfront cash to build this tool and they promote us to possible customers.

The problem was that instead of one kick-ass product we ended up with three mediocre ones. Nobody buys or downloads mediocre products.

It’s better to turn down feature requests and instead create the core of an amazing product. This takes more precision, but over time it’s actually less effort and more fulfillment than managing a bunch of crap.

9. Don’t ignore the money metrics.

Early on at Campground Booking, we switched from a monthly recurring charge to a transactional fee. We’d signed up a few beta campgrounds who paid us $50/month and shortly after they went live, we realized how much support and energy they required to maintain.

The options were: charge them more OR give them our software for free and instead collect a fee their customer pays upon booking.

We spoke to them about it and they all loved the idea of getting the software for free. We saw that each of these parks was taking hundreds (and sometimes thousands) of bookings, so we loved the idea of being able to make significantly more per customer.

The revenue switch worked out great once we implemented it. Instead of a few hundred dollars per year per customer, we could now make thousands. With each new reservation, we’d collect a $5 fee.

However, this model had a flaw.

Customers could sign up and spend months on the platform without ever taking a booking. We also had some customers use the system to only take manual (phone) reservations and never enable their online bookings (which is where we collected fees).

Long story short, we were spending money and time to onboard customers who we hoped would eventually give us money, but with no guarantee.

This is okay to do when you have millions of dollars in funding, but we did not.

It’s also okay to do when you’re building a marketplace like Airbnb because the sign-up and onboarding are completely automated. No Airbnb employee is setting up Zoom calls with you to help you set up your house to rent. With less tech-savvy businesses, we were providing Dunder Mifflin quality service for new clients.

This costs money. Money that sometimes came in and other times did not. We had a revenue model problem.

The problem with not knowing exactly how much a customer is going to pay you is that it becomes challenging (or near impossible) to know how much you should pay to acquire that customer. If a customer pays you $5,000/year, you can spend more to acquire them than if they only pay you $500.

In my next startup, I will focus on finding a revenue model that truly works. Knowing how much a customer is willing and able to pay is critical for forecasting growth. Without these numbers, you are just guessing.

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END OF A VERY LONG EMAIL.

I think I've said this before, but whew. That was a long email. It's been on my heart for a while to write down some of those lessons. I hope at least some of them hit home with you.

Running a startup is not for the faint of heart, but it's also a great way to impact way more people than yourself, solve pain points and push yourself to do things you didn't know you could do.

Now that I'm looking forward to what is next, I'd love to hear what kind of cool business or startup you're currently working on. If you read this far and don't have an active project, I'd still love to hear from you.

Hope you have an amazing day,

Heath