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It Won't Be A Straight Line: A Founder's Journey Starting Growing And Selling A SaaS

Garrett Dimon

Head of Growth, Wildbit

Husband. Father. Work at @wildbit. And past curator of @sifterapp. Also, LBKA.

Crested Butte, CO
Garrett Dimon

You'll learn:

  1. one
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  3. three

Garrett Dimon

Garrett started Sifter in 2008 "because the world needed yet another bug tracker." In the years following, he went through a long medical struggle that ended in getting his leg amputated. He later sold his company and started working for Wildbit - the company behind Beanstalk, Postmark, Deploybot, and Conveyor.

In this talk, Garrett talks about the lessons he learned running a bootstraped company while going through this major life event.

Garrett has had a rough 4.79 years. He's lost 120 days - 6.8% - of the last 5 years. That's like sleeping 1.63 hours less every night for five years.

SETTING THE STAGE - be ready for curveballs

"Bootstrapped issue tracking application loses customer data, shuts down quickly" was the headline Garrett expected to see after accidentally deleting 8 hours of customer data.

In the early days of running Sifter, Garrett accidentally deleted 8 hours of customer data. He thought this mistake was serious enough to end his business and make him the laughing stock of the bootstrapper community.

The actual fallout wasn't nearly as bad as he'd imagined. His customers were beyond understanding, and most of the mistake was recoverable. From this early small mistake, Garrett learned that responding beats reacting - when things go wrong, it's important to take the time to focus on what you can affect instead of panicking.


You may have an idea, but you don't want to spend a ton of effort figuring out if it's good enough.

You have to get to point where where people will give you money. The faster, the better.

Approach everything with baby steps. Never go all-in on your first attempt. Build enough to justify payment and learn. Then build the real thing.

Just like how you probably shouldn't take a triple hit of morphine, there's always something bitesized you can do on your business.

Stripe, MailChimp, WordPress, Zapier, and Airtable make it possible to build the first several version of a web application without code.

Sales is research. Talking to potential customers kills two birds with one stone. Then use that to iterate on your offering.

Version 1 (of Garrett's Leg)

Let's try the simplest solution.

Recurring revenue from Sifter was an amazing form of disability insurance. It was easy to be scared of health issues, but recurring revenue makes it easier.

Pivoting: We learned a little. Some stuff worked. Some didn't. It's time to get serious.

Garrett read Unthinkable by Scott Rigsby going through negative visualization. This dude won the Hawaiian triathalon. The worst case isn't that bad!

Maintain perspective. Not "Well. It could be worse." But rather "I can handle this."

Version 2.0 (of Garrett's Leg)

We feel confident that the best step is to invest in a more ambitious solution.

Garrett committed to what was supposed to be an 8 hour surgery and ~1 week in the hospital. It ended up being two 10 hour surgeries and 3 weeks in the hospital.

He learned that tiny steps are still steps. The key is that they're your steps. Don't compare your rate of progress to anyone else. (Or to "past you."). The challenges you're facing are uniquely yours. Don't get distracted comparing your journey to anyone else's. Or even past you.

Version 2.0 of Garrett's leg was a "free flap" (a skin graft + a chunk of ham from Garrett's thigh), but it didn't work.

Garrett learned to trust and delegate. Don't give up when your first attempt doesn't go well. In our personal lives, we don't hesitate to trust experts, but with business, too often we try to go it alone.

Even though Garrett's doctor wasn't confidence inspiring, he was the best person for the job. There was no way I was going to give up and try to do it myself. Yet, in business, all too often, that's what we do. Delegation is a learned skill, and it's inherently dependent upon both the delegator and the delegatee.

Version 2.1 (of Garrett's leg)

Any major effort is going to run into issues and need some follow-on work. Garrett's doctors had already taken one flap from my left leg. They'd need to get another flap. This meant an extended stay in the ICU. 🏥

He did get a magic morphine button 🔘💊, but his heart rate would go below the alarm level when he tried to sleep. Pain killers. No sleep. Barely eating. A couple of panic attacks. He was in bad shape.

It was at this point that Garrett reached out to Chris and Natalie (the founders of Wildbit).

Progress isn't automatic. Growing pains are real. At some point, growth will plateau. "If you build it, they will come." Right? Nope. Growing a business takes deliberate and directed action. Even then, it's slow.

Garrett learned that growth is just a formula. You have to look at growth and plateaus as simple formulas. Then set goals accordingly. When your business isn't growing, it's easy to question literally everything. However, you have to remember it's just simple math. And that math can tell you exactly what you need to work on. The good news is that you can see these limits coming a mile away. They should never surprise you.

When your business isn't growing, it's easy to question literally everything. However, you have to remember it's just simple math. And that math can tell you _exactly_ what you need to work on.

Garrett learned to work on the right things. The likelihood of working on the right things correlates closely with what customers are telling you combined with your actual growth numbers. Choosing the right things to work on will always be difficult. However, if you understand this formula and break it down, you have some built-in guidance from the business about where you should focus your efforts.

How do you grow? One of:

  1. Reduce Churn
  2. Increase Conversion
  3. Increase Traffic

Physical therapy is a great metaphor for business. I've spent an inordinate amount of time in physical therapy, and it's very cyclic. It's about cycles of pain, improvement, plateaus, and making the adjustments to push through the plateaus.

It's the same thing with our businesses or careers.

When you first learn a new skill or set out on a new path, it's really difficult. Then it gets easier. Then you get comfortable.

You constantly have to push yourself outside of your comfort zone in order to grow.

This is especially true running a business. With each new achievement, you're going to be playing a new game. You have to adjust.

Pain and discomfort are part of the process. Go right up to your limit. Push past it. Suffer a little. Then do it all over again.

Step back and assess

How are you doing? Are you meeting your goals? Do you need to try something new?

For Garrett, it was a major surgery. In business, it may be a major feature release. As things change, it's important to revisit them and take a critical look at where you're at.

For Garrett, recovery plateaued, and his foot wasn't back in the right position yet.

He learned to focus on tangible goals rather than long-term dreams. Let your dreams light the fire, but remember that incremental and measurable goals are how you really get there.

For him, the dream was being active again. Playing basketball. Snowboarding. Running. Going hiking or camping with my family. The goals were much smaller: Walk a single mile. Run a single mile. Run a 5k.

In business, it's the same. Having your business support you full-time is a dream, not a goal. Finding 5 more customers is an actionable goal. Don't worry about two years from now. Focus on here and now, and two years will get here fast.

Make big decisions

Turning points are never easy, and the answer is rarely obvious.

You will face turning points where you have to make big decisions. For Garrett, it was an ankle fusion or amputation. Fusion effectively meant no running or jumping ever again.

Lesson: protect your focus for the things that really matter, and always work deliberately.

Don't avoid big decisions because they're hard. Put your head down, do the research, decide, and then execute ruthlessly.

Elective amputation is about as scary of a decision as you can make. The permanence is really all that makes it scary though.

The good news with business is that nothing is permanent. You can always go back and fix it.

Garrett's ankle. Out of position. Arthritic. He talked to 4 surgeons, and they all advised an ankle fusion.

So what's the deal with amputation again? Just how active can you be? What are the limitations? Thanks to the books and talking to other amputees, Garrett wasn't scared of amputation.

He was scared of the permanence and of being wrong, but he was at peace with it pretty quickly.

All of the amputees he talked to had regret. Specifically, they had one regret…

…the exact same regret.

They wished they had done it sooner.

At this point, Garrett and his wife had their second daughter. He was still running Sifter effectively by myself.

The idea of another major surgery at this point means a lot of burden on Lauren to take care of her family.

Fusion would theoretically be a quicker recovery (~3-6 months) with fewer short-term restrictions.

Amputation would mean pushing a lot onto Lauren for the foreseeable future. (~18 months to a full recovery)

This is a nerve-wracking decision. Amputation felt like it had the best potential for a good long-term outcome.

Fusion felt like the safe and responsible thing for Garrett's family as a whole. Yet. With amputation he saw liberation. With a fusion, he only saw shackles.

And so they put screws in Garrett's foot. It was the safe play. He originally thought it would be a 6-month detour at worst. They ended up giving it (and other treatments) 18 months.

Screws in Garrett's foot was the safe play

Some time after the fusion, Garrett talked to Wildbit again, but this time, there was a way to move on from Sifter.

The weight of running a business and feeling an obligation to customers for years of neglect was at odds with the same feelings towards family.

Joining Wildbit was key. He was a terrible boss for himself. Wildbit on the other hand is the healthiest workplace he could imagine. It had been absolutely critical to his recovery.

For some decisions, there's not an obvious answer. You may need to make a leap of faith. Do your research, and make a decision. Sitting still can often be worse.

Is it good enough?

After big efforts, launch, and then re-evaluate. Here we are again, only now I had real data on what a fusion was like.

Chronic pain. Middling functionality.

But he could get by, but was "getting by" enough?

The thing about amputation is that it's so permanent. There's no Command-Z. No matter how confident I could have been, it's scary.

He had to have a framework to weight it all.

Garrett questioned what he was capable of. Are those activities pain-free enough to be enjoyable?

He tried playing basketball again, but could only tolerate about 30 minutes.

Soon, the pain and disability from ankle fusion was bad enough that Garrett started to see that amputation would be better for his family too. It was clear that if functionality was important to Garrett, the fusion wasn't going to cut it.

Around the same time, after spending 8 years on Sifter and having it financially support him, he sold it. Sifter was in good hands, and he could finally focus more on his recovery or maybe amputation.

Don't count on data and logic to provide the right answer. Too often we try to be 100% confident about decisions that require a leap of faith. These days, there's so much talk about A/B testing and data. That stuff's useful, but you can convince yourself of anything.

Moreover, in the early days of a business, you won't have statistical significance.

Taking the next step

Once you've handled the basics, the real work begins.

~5 months from deciding to amputate to actually having it. Schedule/rescheduled a couple of times as we tried some other options.

Opportunities to cancel it kept popping up, but I finally said "enough."

Waking up with just one leg

It's ok to let go. Just because something is holding you back, doesn't mean you have to hold on too.

The journey never ends

There will be milestones, but there's never a finish line.

Six months after amputation, Garrett spent two and a half days snowboarding without pain killers. Today, he can comfortably enjoy a full day on the mountain.

It's about progress—not aspirations. Focus on how far you've come because our journeys never end. You'll never reach a finish line.

Garrett isn't where he used to be, and he's not quite where he wants to be, but he's getting there every day.

When you're recovering from injuries, you go to physical therapy. When you're recovering, you have a physical therapist. When you're building a business, you find an advisor.

Find your people so they can nudge you along safely. When you're in the thick of it, it's difficult to know if you're pushing yourself too hard or not hard enough.

Garrett's ability as an amputee

Garrett's mountain biking/snow boarding foot has countless adjustments

Don't adjust too many variables at once. With business, you have a ton of dials you can adjust, but only a few matter. Focus on deliberate calibrations rather than random adjustments.

Garrett can't tease his wife about bringing a suitcase worth of shoes anymore when they travel

You may put on sunglasses or grab an umbrella. Business and life is no different. We can all be confident our circumstances will change. So when it changes, do what humans do. Find a way to adapt.

We're all adaptive. Adaptation is unavoidable, and businesses have to adapt and change too.

What we're adapting to is different. For some it's losing a leg. For some it's having kids. For others it's a new role at work.

You're way more adaptive and strong than you realize. You've just never had to unleash that strength. It's there. You just don't know it yet.

With that, I want to leave you with one thought…

We all face struggles, but it's never really about the struggles. It's about us.

Or, more specifically, it's about what we're truly capable of.

So, next time you're facing a mountain, real or figurative, take a step back.

Take a deep breath. Let that mountain light a fire in you.

Have faith in your strength, and go conquer it.


What markers do you give yourself to know that you're on the right path?

Explore a bunch of things to figure out what the right thing is to focus on. Even then, there are no guarantees. Find the thing you want to focus on and make sure it's fulfilling and will make money.

Our public personas are all very cheerful. How did you shape your persona through tragedy?

I tried not to let it affect my customers. The product would stagnate for a few months at a time, but it was never significant enough to explain.

For more, check out Garrett Dimon's free book, Starting & Sustaining, and podcast of the same name.

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