It Won’t Be a Straight Line: A Founder’s Journey Starting, Growing and Selling a SaaS

It won't be a straight line

Raise your hand if everything in your life has gone exactly according to plan? Over the last 5 years, I’ve had a lot not go as planned, and I learned a lot about rolling with the punches.

Now I’d like to share some of those lessons. In most cases, this kind of wisdom costs an arm and a leg, but I got it half price. And now I’d like to pass it on to you at a deep discount. (Note: If you’re reading this instead of watching, I’m a left below-knee amputee. That’s kind of important for this joke to make sense.)

Hi, my name is Garrett Dimon. A couple of years ago I decided to sell my SaaS business to focus on my health, and then a few months after that, I decided to remove my leg.

The intersection of these two events helped me see quite a few things in a new light.

But, before we dig into the topic, since I know there’s one question on everyone’s mind, let’s go ahead and get the elephant out of the room…

I did briefly consider working at IHOP, but ultimately decided it would be less lucrative than SaaS.

It’s been almost 5 years.

Almost 2 years since amputation.

I’ve spent a lot of time dealing with this, and I will for the rest of my life.

As a side note, these days, after going through all of this, there’s really only one thing that I’m truly and deeply afraid of. I have to pay close attention and enunciate very clearly when I tell people I’m going to see my prosthetist.

Imagine losing almost 2 hours per day for four years. (Admittedly, most of that was condensed into ~6 months, but it’s still ongoing.)

I played a lot of basketball. I sprained my ankle a lot. I didn’t take care of it because I could never wait to get back on the court.

I believe that’s called “foreshadowing.”

Other than basketball, I kind of fell in with computers, and in particular, I became fascinated by the wide variety of processes and how different teams handled things like design, development, and quality assurance.

There’s a joke that I feel perfectly summarizes why this was so fascinating to me…

A group of ten top software engineers is sent to a class for aspiring managers. To start the class, the teacher walks in and poses a question to the group:

"You work for a software company that develops avionics software for airplanes. One day you are taking a business trip. As you get on the plane you notice a small plaque that indicates the plane is using the software your team developed. Who would get off the plane?”

Nine of the ten developers immediately raised their hands. The teacher looked at the tenth curiously and asked, “You would stay on?”

The engineer shrugs and replies, “Sure.”

Impressed, and a bit dumb-founded by the confidence, the teach asked for an explanation.

To which the engineer replied, “Simple. If my team wrote the software, the plane wouldn’t even get off the ground."

All teams are dysfunctional in their own way. So, I spent a lot of time thinking about that. After a lot of thought and careful innovation, I came to the obvious conclusion that the world needed yet another bug tracker.

By itself, Sifter isn’t particularly unique, but in the context of running a SaaS business through medical struggles and then selling the business, it’s more interesting. Due diligence sheds an incredible amount of light on things and helps uncover screw ups.

Sifter will 10 years old December 2018.

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I also wrote a book to pull together all of my advice and experience. The book is freely available on the web. As is a projections worksheet.

Now that’s evolved into a massively updated and expanded second edition and a podcast interviewing other founders not about success, but about trials and tribulations.

After Sifter, I joined a small company called Wildbit. Joining a team where the burden wasn’t entirely on me was huge.

It’s easy to get carried away with doing your own thing and glorifying independence, but it’s not always the right path.

If you’re not familiar with Wildbit, you might be familiar with our work…

• Beanstalk
• Postmark
• DeployBot
• Conveyor

Be ready for curveballs. Things have a funny way of not always working out exactly the way you’d expect. This was true with both Sifter and my health.

I had a minor surgery and went home with one of these ice machines. At my first followup, my doctor unwraps my foot and there’s some frost bite. I had no idea what I was in for in the coming years, but I was at ease. I wasn’t really worried about it.

Somehow, I was able to maintain that over the years.

People often ask about my generally positive attitude and outlook. The thing is, it’s actually pretty easy—unfair even—but I literally can’t help but start every day on the right foot.

Seriously, though. This is easy to joke about, but there have also been plenty of challenging days. They still happen, but I really focus on the steps that are under my control.

I’m going to jump ahead to a story during Sifter that really helped me understand this…

In the early days of Sifter during a server upgrade, I had a decision to make that was moderately time sensitive.

In a hurry, I made a bad choice and deleted 8 hours of customer data. If I had stopped to collect myself instead of acting quickly, I wouldn’t have made the mistake.

I knew Sifter was going out of business. In my head, this is what I expected to see the next day…

So, with nothing to lose, I took a stab at salvaging the situation. Having nothing to lose is really quite liberating.

Ultimately, it cost about $700 in service credits, but everyone was actually really understanding.

Put into simpler words…

There’s always something you can do even if it’s as simple as giving yourself permission to slow down.

If there’s one thing to remember in the early days, it’s that action and momentum are priceless.

You can do so much without writing a single line of code. You don’t necessarily have to even show it to customers. Build a back-end or prototype just for yourself to begin to understand the scope of what you want to create.

By doing work, ideas will come to you, and you’ll begin to understand the scope of what’s in your head.

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.

After the frost bite discovery, my foot started to thaw, my pain was out of control, and we went to the emergency room.

The doctors didn’t just flood me with pain killers. They tried one round. Waited 15 minutes. Then another round. Waited 15 minutes. Then, the third round worked.

It was something like this…

Thankfully, Lauren had the presence of mind to capture this for posterity.

You don’t have to know that it will work. You only need to know if it can work.

Start manually. Use modern tools. Try to build something of value without writing code. This is precisely how Derek Sivers started CD Baby. Everything was incredibly manual, and he just improved processes when they became too much to handle.

By doing this, you’re learning with very low risk and even lower costs. It’s a pain in the ass, but that’s how you figure out what matters and what doesn’t. You’re also uncovering complexity. This forces you to focus on the value you’re providing rather than the challenge of writing code.

People say no to your web site every day without giving you an explanation, but when you talk to them in person, they explain.

It was a quick in and out surgery. Not much to it.

Can it heal itself? Hyperbaric chamber for 7 weeks x 2 trips per week x 2 hours each.

I had a ton of time to think. Unfortunately, not enough.

Doctor appointments. Hyperbaric treatments. Pain killers. Sleep. Wound vac changes.

My responsibilities to Sifter started to slip, and I was a terrible boss to myself.

I began to question how Sifter fits in to everything.

I can’t repeat this enough. While it may be slow to build a recurring revenue business, once it’s built, it’s incredible.

I even got a raise while I was on “recurring revenue disability” because Sifter was still growing.

Things were kind of working, but not enough. We needed to explore more aggressive options.

I did some negative visualization. What’s the worst case scenario? What would life look like with an amputation?

So I found this book by Scott Rigsby, the first double amputee to complete the Hawaiian Ironman Triathalon.

It was a great read at the right time, and it helped me realize that even if it came down to amputation, I could handle it.

I’ve found “Well, it could be worse” to be the most useless saying. Of course it could be worse, but that doesn’t mean anything.

You’re going to deal with a bunch of crappy things in business. Just understand that you can handle it. Take a directed approach, and solve the problem.

I 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.

(Side note: You can do support for a SaaS app from a hospital bed while on narcotics. Just not really in ICU.)

We all have our own challenges and demons. It’s easy to feel like they’re either insignificant or insurmountable.

The challenges you’re facing are uniquely yours. Don’t get distracted comparing your journey to anyone else’s. Or even past you.

In the early phases of anything, even a small win is significant. It’s a moving target.

If a skin graft is bacon, a free flap is a big chunk of ham. Unlike a skin graft, they need to get that chunk from somewhere.

In my case, it was my thigh.

So, doc does the free flap, but shortly thereafter…the words you don’t want to hear from your a doctor while evaluating you…

Within a day or so, it was clear that the flap wasn’t getting enough blood flow and wasn’t going to make it.

It was at this point, I ask “Are we throwing good money after bad?” (Openly implying that I was alright with amputation.)

To which, you might expect a surgeon to respond with “Don’t worry, this is going to go great.”

Instead, he said,“Don’t worry, there are plenty of places I can take the flap from.”

Even though he 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.

So they had already taken one flap from my left leg. They’d need to get another flap.

This meant an extended stay in the ICU.

If you’ve never been in ICU, it’s rough.

Wires are running everywhere. Things are beeping. You can’t get out of bed. Our daughter was two at the time, and children aren’t allowed in ICU, so she couldn’t visit.

Given the shape I was in, I’m not sure it would have made sense anyways.

But they do give you a magic button.

It did help, but my time in ICU went from being in pain to just being all around miserable.

I was pushing the button simply to not deal with it.

The big problem for me was that your average resting heart rate is about 60 bpm. They monitor your heart rate and have alarms that go off if you drop below 40 bpm.

My resting heart rate is closer to 45. In most contexts, this is a “good thing,” but in ICU, it’s complicated.

The thing is that pain killers lower your heart rate. And when you fall asleep it goes down a bit more.

So for me, whenever I started to fall asleep…

The outcome was an alarm that effectively went off whenever I went to sleep.

Pain killers. No sleep. Barely eating. A couple of panic attacks. I was in bad shape.

I’m ready to get out of there. So…

A little drugged up at this point and completely exhausted, I ask, “how much longer will I be here?”

Their response…

“The floor?!?! What the hell kind of hospital is this?!?! Only ICU has beds?”

Turns out “the floor” is just hospital speak for the non-ICU rooms.

In the meantime, it’s October, and our daughter is about to have her first meaningful Halloween. This is what I’m missing…

What started as “how can I get back to playing basketball” evolved into “how can I get home for them.”

I think similar things happen in business. The reasons we had for starting the business—freedom, independence, flexibility—fall by the way side. We focus on the wrong things, and it gets away from us.

It was this point, while I was still in the hospital that I first reached out to Chris and Natalie—the founders of Wildbit. I was starting to question whether self-employment was right for me at the moment.

It was a constant struggle to figure out whether I was chickening out or whether it was the right thing to move on from Sifter.

Nothing happened at the time, but it opened a very important door.

“If you build it, they will come.” Right? Nope. Growing a business takes deliberate and directed action. Even then, it’s slow.

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.

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.

Ideally, you’ll fix the leaky bucket before you throw a bunch of traffic at it, but if your skillset means you’re really good at throwing traffic at something, that can help give you statistical significance.

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.

Don’t run from pain and discomfort.

Most pain and discomfort is really just growth in disguise.

For me, 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 me, recovery plateaued, and my foot wasn’t back in the right position yet.

When I talk about pain, imagine a really bad ankle sprain combined with arthritis, and it never stops.

It only gets worse as you do more.

For me, 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.

You will face turning points where you have to make big decisions. For me, it was an ankle fusion or amputation.

Fusion effectively meant no running or jumping ever again.

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.

This is my ankle. Out of position. Arthritic. I talked to 4 surgeons, and they all advised an ankle fusion.

I had researched ankle fusions already, and this intuitively felt worse than amputation. They’re practical, but functionally, they’re more limiting.

I’d probably never be able to run or jump again, but maybe I’d be pain free.

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, I wasn’t scared of amputation.

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

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

…the exact same regret…

They wished they had done it sooner.

At this point, we had our second daughter. And let’s not forget that I’m 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 all of us.

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 our family as a whole. Yet. With amputation I saw liberation. With a fusion, I only saw shackles.

Me - “Doc, if I fuse, will I be able to dance?” Him - “Yes.” Me - “That’s awesome because I never could before.”

And so they put screws in my foot. It was the safe play. I originally thought it would be a 6-month detour at worst.

We ended up giving it (and other treatments) 18 months.

Some time after the fusion, I 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. I was a terrible boss for myself. Wildbit on the other hand is the healthiest workplace I could imagine. It’s been absolutely critical to my recovery.

While less directly relevant here, the point is that some decisions will be difficult.

Here we are again, only now I had real data on what a fusion was like.

Chronic pain. Middling functionality.

But I 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.

I had to have a framework to weight it all.

What am I capable of? Are those activities pain-free enough to be enjoyable?

The first was a simple test. Could I move around comfortably on a basketball court and enjoy myself?

It might look like it, but what you can’t see is that I couldn’t run or jump off of my right foot at all, and I could only tolerate about 30 minutes of this.

I knew I’d never play again with a fusion…

Would I be able to do the things with these three that we’d all want to do?

Then the pain and disability from ankle fusion was bad enough that I started to see that amputation would be better for them too.

I could live with not playing basketball, but if I couldn’t do that, all I could do was wonder what it would mean to my family.

Skiing and snowboarding was something we could all do together…

Before my fusion, I was able to get almost a full day in. It took a couple of heavy duty pain killers, but I did it…

This time around, I barely made it down the mountain. That night I went home, and it started to sink in…

About the exact same time, a friend was literally summiting Mount Kilimanjaro without either of his legs. And none of his fingers.

I can barely slide down a mountain, and he’s climbing up one.

It was clear that if functionality is important to me, the fusion wasn’t going to cut it.

Around the same time, after spending 8 years on Sifter and having it financially support me, we sold it.

Sifter was in good hands, and I cold finally focus more on my recovery or maybe amputation.

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.

~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.”

Completely at ease going into surgery.

Waking up with just one leg.

This wasn’t just the drugs. (They hadn’t kicked in yet.)

You find ways. Oddly enough, this was one of the first times I felt like I was just able to have fun without pain.

Letting go has as much to do with me selling Sifter as it does with some individual ideas. Sometimes we hold on way too hard without a solid reason.

It could just as easily relate to what you’re doing currently. Should you let go and move on to whatever is next for you?

So where are we at today…

Like running a business or recovering from a major surgery or disability, it’s never really over. There’s no finish line, and it’s unhealthy to think about things in terms of one.

These were my first steps. They were incredibly painful, but that’s pure ecstasy you’re looking at.

Just out of frame is our oldest. She was two when this started. She had been asking me when I’d be able to run with her for months.

So naturally, I just took a handful of steps, and she asks…

“Daddy, can you run yet?”

Within a few months, that question changed to…

“You can’t beat me!”

…and then not long after, that gave way to…

“Daddy, you’re cheating!”

This was the first time it clicked that I could run again.

I had run on a treadmill in physical therapy, but I wasn’t confident enough to trust my leg if I didn’t have something to grab on to.

This is me 6 months after amputation. I spent two and a half days snowboarding without pain killers.

Today, I can comfortably enjoy a full day on the mountain.

I’m not where I used to be, and I’m not quite where I want to be, but I’m getting there every day.

I’ll bet you’re in a similar place. You’ve made progress, but you’re not where you want to be.

Just make progress. Then look back.

When you’re recovering from injuries, you go to physical therapy. This is my physical therapist, Matt.

When you’re recovering, you have a physical therapist. When you’re building a business, you find an advisor.

Find people to help push you just hard enough.

This isn’t just my story, the case of one freak amputee who ran again.

I’ve met so many amputees doing things that they never did or even considered before amputation.

When I go mountain bike riding and people see my foot, they say “That’s so cool! I want one!”

On that mountain biking/snow boarding foot. There’s countless adjustment to make just to the foot.

This is a lot like business.

LESSON: 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.

The thing is, I can’t tease my wife about bringing a suitcase worth of shoes any more when we travel.

⛸ E F G H I J I change feet. 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.

I ran a 5k. I’ve never run a 5k. I never even thought about running.

When I shared this, the best comment a friend was made was pointing out that I beat the little girl with two legs. “Take that, little girl!”

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.

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