How 2017 Completely Kicked My SaaS

An unconventionally epic bootstrapped startup year in review.

Just another year in the life of a wild-eyed, do-it-all-yourself bootstrapper…

For most of us, 2017 was a year better left in the dumpster fire from which it was born (aka, “ 2016”).

For me, 2017 was something truly remarkable and special that I’ll soon not forget — just like how I’d imagine contracting a mild case of necrotizing fasciitis might be.

If “growth is painful”, then 2017 left me feeling a bit like a bootstrapped startup remake of House.

Between running a growing portfolio of bootstrapped startups (including Tamboo, an all-in-one session recording and replay tool), writing a book about bootstrapping startups (while still adding to my growing Medium epic, which has now been read by over 180,000 people!!!), building a Slack community for bootstrappers, entertaining all the awesome people following me on Twitter (and adding over 500 new followers organically), getting ready to launch a new podcast, starting an open source SaaS-in-a-box, training for an upcoming 100 mile ultramarathon, reading 38 non-business books totaling 19,627 pages, and answering over 766 emails from fellow bootstrappers the world over (all while still having “a life”), you might be thinking that I “crushed it” in 2017.

Put that way, yeah, I guess I kicked some serious ass.

But in the process, I also got my ass seriously kicked.

But maybe I’m getting ahead of myself here. Maybe we should rewind things a bit and start at the beginning…

December, 2016

It all started on December 19th, 2016, a day that will go down in infamy.

That was the day that I inadvertently broke the internet and set off this whole sick cycle carousel I’ve been riding ever since.

On that day, the stars, constellations, git branches, and quantum bits all somehow aligned (in what I can only describe as some kind of weird prank I’m still convinced the universe is playing on me) and plucked me from my comfy and cozy “lurking in the shadows” bootstrapped existence and unceremoniously plopped me down on the Mount of Startup Olympus (otherwise known as “Hacker News”).

Now, for most people, getting to the top of Hacker News (and all of the accompanying attention that ensues) is a wet startup dream come true.

(And I’m not going to lie— that whole experience definitely creamed my Twinkie a little.)

But truth be told, it’s been both one of the best things and one of the worst things that’s ever happened to me.

Before we dig into that though, I think it helps to share a little bit about what 2016 was like for me up until that point, which is something I haven’t shared with anyone to date (see, you’re special!)

Simply put, 2016 was rough — both personally and professionally for me.

I had a handful of projects flame out pretty much simultaneously, including one that was my oldest source of revenue, as well as another that was my (at the time) largest source of revenue.

I threw everything I could at them to try to bring them back from the startup graveyard, but try as I might to rescue and resuscitate them, I just couldn’t make their shit beep like it used to.

Admitting that they were “done” and that it was most likely time to kill them off was one of the hardest things I had to come to grips with.

That, and realizing that all of this represented a 45% hit to my income.

I’ll admit — I was not the funnest person to be around at that point in time.

In fact, I pretty much just shut down.

I couldn’t really deal with much of anything.

Just trying to figure out what to eat for dinner would send me into an hour-long cycle of analysis paralysis (I kid you not).

To offset all of this lovely stress, I started running my ass off even more than I normally did. That is, of course, until I broke three of my toes and wound up with a crippling instance of achilles tendinitis that put me out of commission for months.

After taking some (well deserved?) time to hit rock bottom and feel sorry for myself, I decided to pick myself back up and stare into the abyss looming back at me.

If I gave up, I knew that I could never forgive myself.

And I knew that if I didn’t stare down this existential beast staring back at me, that it would tear me apart limb from limb.

So I dug in and got myself right again.

I couldn’t run, so I started meditating regularly (which was brutal at first). I stopped listening to post-hardcore music (quite arguably my drug of choice) and switched full over to tropical house. I started reading fiction and literature at night (sometimes going well into the morning). I started eating lighter (and cheaper). I forced myself to be brutally honest about my feelings — and sought to destroy them before they could destroy me.

And most of all, I forced myself to go “back to basics”.

After I had calmed myself down, I realized that I had probably prematurely torched a couple of the projects that I had taken behind the woodshed and that some of them could have probably been saved.

Of course, it was a little bit late for that now.

So rather than cry over spilled milk (or slain startups), I forced myself to shore up what I had left and to grow out what I could.

Once I had gotten myself back on solid ground, I had a renewed sense of clarity from the whole experience.

It was from this “back to basics renaissance” that I penned the first part of The Epic Guide in order to start the fulfillment of a vow that I had made to myself.

Two months later, it took off. And the rest is history.

That was 2016.

Enter 2017.

We *were* warned…


So I ended 2016 on a high note that appeared to be the harbinger of awesome for what 2017 would bring — or so I thought.

Looking back, January was actually rather foreboding in a way — I just completely missed the signal from the noise.

Much of January was spent trying to dig myself out of the fall out from having gone interstellar in December.

My inbox was flooded with emails.

I had more Tamboo signups in trial than I could keep up with.

And of course, this crazy idea for turning The Epic Guide into a full-length book was getting traction and picking up steam.

I remember January as “inbox month”.

Whether it was responding to people writing me about the articles, going back and forth with people interested in the book, or sending gazillions of emails to all of the people who were trialing Tamboo to see how I could help them, if I could get feedback from them, or if they were at all ready to convert to a paid plan, I just remember lots and lots (and lots)… of emails.

January ultimately ended on a disappointing note: Despite the massive influx of new trials, and despite all of the emails that I sent, people just weren’t converting like they should have. Part of me knew this would happen. I knew that these were just “tire kickers” checking out Tamboo from the Medium articles and that they were never serious about paying — they were just curious and wanted to play. And since it was free to try out and play with, they did just that. (Much to my chagrin.)

But that still didn’t stop me from hoping that that wasn’t the case and it most certainly didn’t stop me from trying to turn those trials into paying customers. In my exuberance, I even broke the cardinal rule of product management and added features requested by customers who said “It needs to do this before I’m willing to pay”. And of course, despite spending weeks building those features out, none of them converted or paid once they were in place.

And so it begins…


I wish I could say that I stopped foolishly chasing the influx of new trial users in February that I secretly knew where just bad for business, but then I wouldn’t be sitting here kicking my own ass for your amusement, now would I?

Instead, I spent a ridiculous amount of time fucking with Tamboo’s UI and UX to see if that would somehow convince them to stay.

Fucking amateur hour, right?

(Stay tuned kids, it gets better.)

It’s about this time that demand for The Epic Guide: The Book reached critical mass. I had to make a decision — it was time to shit or get off the pot with this book “idea” I had.

Part of me really, really, really didn’t want to do this book.

Part of me knew that this would probably turn into a “bad idea” that I would regret.

Part of me was like “Are you nuts?! This is going to be a huge time sink and distraction!”

And yet there was that nagging voice in the back of my head that said “If you don’t take this opportunity you’ve been given and run with it, you’re going to regret it.”

I hemmed and hawed about it for weeks on end.

Eventually, I literally flipped a coin to decide if I was going to do it or not (I kid you not).

Fucking heads.

And no, it wasn’t a trick coin.

So I spent the better part of the end of February coming up with copy and building out the presale site for the book, hooking up payment processing, and getting Part 4 of The Epic Guide ready for launch, where I would announce the launch of the presale.

And of course, the damned thing had to take off.


March was kind of all over the board.

I did a lot of work on Tamboo, from adding features to updating the marketing site to tweaking the backend. I think this was around the time that I did the first major rewrite or update of the heatmap engine, as well (more on that fun later).

In addition to the book presales continuing to pile up, March is also when Courtland and I recorded my Indie Hackers podcast episode.

I don’t know if you can tell or not from listening to it, but I was super the fuck freaked out.

The IH podcast was newer at the time (I was episode #9), but I knew it still had massive reach even then — and that that reach was growing every day.

I had never done a podcast episode or even a recorded interview for that matter before — and here I was doing my first podcast interview ever on Indie Hackers?!

March was also when I started Bootslacking, an invite-only Slack group for people running or starting bootstrapped startups. This was mainly born out of a frustration of not having any good place to “talk shop” with other bootstrappers, and since I was getting emails from so many of them, I thought it made sense to bring them together in a forum where the focus could be on sharing and learning knowledge and experiences about startups and business — and where anyone who turned out to be a random fly-by-night startup promoter would be immediately booted.

Meanwhile, The Epic Guide continued to grow and and spread its tendrils across the internet, creating an obscene number of “tire kicker” free trials that I (of course!) was still running around trying to turn into magical unicorn poop conversions.

These fucking tire kicker trials…


I remember April vividly, despite the complete lack of sleep.

April is when things really started to heat up.

It all began with the build-out of a “live demo” for Tamboo.

The idea for the live demo was simple enough: It would let people try out Tamboo on their own website in a quick interactive demo that wouldn’t require them to install anything so that they could see how it would work. Basically, they’d enter their website URL, I’d show them their website in an iframe, I’d record what they did, and then I’d let them watch a recording of that session.

On my end, this would hopefully:

  1. Discourage tire kickers from signing up for a trial — they’d be able to see what Tamboo did in the live demo and hopefully have their curiosity squashed if they weren’t serious.
  2. Encourage signups from people who saw Tamboo in action and wanted to use it on their website — essentially giving people “a taste” in order to help incentivize them to create a trial.
  3. Give me inbound leads to make my sales efforts a little easier (via the website entered). Rather than having to rely almost solely on outbound prospecting, I could add some interested inbound leads to my pipeline and close some more sales.
  4. Give me data about what kinds of websites were using the demo and converting or not converting. I was hoping to find some kind of trend in the type of websites which were more likely to convert vs. not convert to help out with future targeting.

Simple enough, right?

From a technical perspective, building out the demo was much more difficult than I had anticipated. It turns out browsers don’t really like it when you try to inject JavaScript into an iframe whose source URL isn’t one that you own (who’d of thought, right? 😐).

So I basically had to build a proxy that would retrieve the website requested and serve up the content from my own domain that I could then inject the Tamboo agent into to do its capture and recording magic. But even that wasn’t as straight-forward as you’d think, given all the websites using CORS to block requests to things like stylesheets, etc. And not to mention all the rewrite rules that you had to apply to things like stylesheets, image URLs, links, etc., etc., etc. to make it all work.

It took me about two weeks of (literally) around the clock hacking to get something that I thought would work together.

Once it was live, people started using it en masse.

And that’s when I realized just how far I was from “getting it right”.

There were so many random ass edge cases that pretty much every site that tried it out wound up having massive rendering and recording issues.

In short, I spent a lot of time sending emails to people to apologize for the shitty demo experience they had while trying to salvage what I could. And all that time, I was madly plugging away around the clock fixes for things that I saw people running into.

Oh, and did I mention that all those beautiful leads and data that I thought I would get were basically total trash?


It turns out a lot of people just liked to stick sites like and whatnot in there to see what would happen (plus there were more than a few cheeky bastards who loved to put URLs in to my competitor’s websites…)

And the sites that did use their actual website address?

Most of them were things like doggy boutiques, hair salons, psychologists, a Hungarian foodie site, florists, and a bunch of (obviously) very early stage “startups”, just to name a few.

There was absolutely no rhyme or reason to any of it. None of them demonstrated any kind of target market pattern like I was hoping to uncover. There was pretty much nothing actionable that could be gained.

And to make things even more fun and interesting? The people who did sign up to view their recordings from the demo hardly ever converted to an actual trial. It was one and done, in and out.

Also in April (oh, we’re not done yet here), I started to hit some massive performance issues and had to completely refactor my backend.

This was something that was slowly growing and coming to a head, but was put over the top by a super large website coming on that singlehandedly threw more traffic at me than I have literally ever seen in my life before.

So with all of this live demo fun going on, I was simultaneously doing everything I could just to keep the lights on while getting buried from more traffic than a Hacker News tsunami — on an hourly basis.

I eventually split out the new customer onto their own dedicated set of servers just to get their load off of everyone else (who were starting to complain about performance) and used the experience to completely revamp the backend.

That refactoring effort required me to do a massive data migration effort that I spent days planning and testing for in my staging environment to make sure it would go off without a hitch.

And of course, nothing went off without a hitch when I ran it in production.

In fact, there were hitches lying all over the floor of my office, broken and shattered as I frantically tried to make things work. Everything was locking up, freezing up, timing out, and taking way more time than my test runs would have indicated.

I thought I had done everything right to avoid this — I had even used a complete copy of my production data to run my tests against.

So what the fuck happened?

Production load.

The live load on the system wasn’t something I had accounted for and basically caused everything to violently thrash in an endless cycle of pain.

After three sleepless nights, I finally was able to pull the system out of its downward death spiral and get the migration to complete.

Three fucking days.

It took six hours in staging.

Oh, and then a few weeks later that massive new customer that I was really excited to have on board that kind of pushed everything to the tipping point of catching on fire and burying me in startup ashes unceremoniously cancelled without reason and went dark. This is of course after having had numerous back and forth emails and phone calls with them to get them properly onboarded, and after they had gleefully declared that everything was working “great” and that it was “awesome” and that the PO was being cut.

As if that weren’t enough, I also wrote the first 100 pages or so of The Epic Guide Book in April, as well as started a major refactoring of Tamboo’s UI and UX, codenamed “Project Cayman”.


May saw the release of Project Cayman, (another) complete refactoring of Tamboo’s heatmap engine, and support for capturing and recording YouTube video interactions (yet another one of those customer requests I probably should have just passed on in hindsight).

I also completely updated the marketing site as well as modified the pricing structure to capture what I thought would have been a good opportunity to align pricing to how people were using Tamboo (which ultimately became yet another failed experiment).

At the time, there was no limit to how many websites you could use Tamboo on under a single account. I saw that a number of people were using Tamboo on multiple websites and thought “Huh! Maybe I should tier the pricing based on how many websites they want to use it on!” I had always hated the usage-based pricing of how many recordings people could have. Most people just don’t know how much traffic they get, or how many recordings they might need. I had done things to try and make this easier on the end user, such as leaving limits open during trials and then recommending a tier based on their trial usage, but I still felt that these “limits” were maybe preventing people from signing up for a trial. So in my mind, this was the best of both worlds — you know how many websites you have or want to use this with, and you don’t need to worry so much about limits then. Brilliant, right?

Yeah, not so much. (But it took over a month to figure that out.)

But honestly, what I remember most from May is how Project Cayman and its roll out just ruthlessly kicked my ass. All of this was a continued attempt to convert all of this “startup gold” traffic coming my way. I was getting people coming through, signing up, trialing, using it daily, and then never converting when it was time to pay (despite numerous outreach emails, many of which received favorable replies like “I love it!”, but then they’d go dark when it was time to pay). And so I continued to think that I had to fix something with the UI and UX to make it even more awesome to get all these people to convert. The conversion rates just weren’t where they should be, despite the large influx of trial users.

So I worked around the clock to “improve” the UI and UX to try and “make it work”. After all, the (small) number of people who responded to my emails about why they cancelled out of their trials all said stuff about the UI and the UX, so that must be what needed “fixed”, right?

Oh! And of course, live demos were still going at this time, causing me endless frustration and grief and somehow bringing even more tire kickers in through the gates. (More on that in a bit.)


At the start of June, I kind of lost my shit.

I think it helps to understand a few things in order to really understand why.

When I had originally written the first part of The Epic Guide, it was just a Medium article that I had written. It didn’t have any reference to Tamboo or anything else. It was just me writing as me.

A number of people were like “What’s your startup?! I want to check it out!”

I thought that was pretty cool and a completely valid request, but at the same time, I was like “which one”?

I had a number of “startups”, and I really didn’t want any undo attention on some of them that I thought could introduce some otherwise unnecessary competition in their space.

So I picked one of my newer ones that I thought was complicated enough that it would turn people off from trying to copy it and that I thought could benefit from some free eyeballs 🙃

Up until that point, I was slowly but steadily growing Tamboo with very specific market segments that worked well with it being a younger platform that still a lot of work ahead of it.

Tamboo was my first attempt at “leveling up” from more niche applications. It was an intentionally more ambitious, more mass market play. It was my “10x” endeavor. And it looked like it had the potential to do just that based on early engagement, feedback, and results.

Now, keep in mind, this is all before the Hacker News tsunami.

People who initially read the articles (again, before the HN kraken) checked out Tamboo (now that there was a “plug” for it), seemed to like it, signed up for it, and even became customers.

And I was like “Wow, this is pretty cool. Non-heavy handed content marketing about a topic that I’m completely passionate about for the win!”

And then the Hacker News tsunami hit (and spread) and all of that went to shit.

Sure, I started getting way more trials, but the conversions were total shit.

Because those people weren’t really my target market.

But there were just so many of them that I just couldn’t keep myself from trying to capture some of that “market”.

Now, the other thing to keep in mind is that prior to The Epic Guide gaining notoriety, I was pretty much a “shadow lurker”. Aside from playing around with answering startup questions on Quora at one point, I really hadn’t ever “put myself out there”.

In fact, I never wanted to be “out there”.

Some people want attention, recognition, notoriety, fame, and so on.

Me? I just want to make money running a business that I own. No muss, no fuss. I don’t care who knows who I am or what I do. I’m perfectly happy making bank and living my life without all of the accolades or vanity that come with running a “startup”.

Okay, so where was I?

Oh yes, the losing my shit part.

Basically, I had spent the last six months chasing some sort of elusive “growth ghost” with Tamboo by trying to turn this “marketing channel” that startup notoriety had given me into something usable, and it just wasn’t working the way that I thought it should.

Combine that with the fact that I was experiencing high churn (about a 3 month average LTV) from these efforts with an app that I had planned on being low churn.

Part of the allure of Tamboo to me was that I felt that it would be something that people would buy and keep for a long time as a way to learn from changes they made to their website, as well as a kind of “insurance policy” they could use to troubleshoot issues that might creep up. I imagined it would be something more like an analytics program that people would use maybe a few times a month but would continue to keep around indefinitely because they couldn’t “go back” to running a business without the kind of visibility that it gave them.

So that was one part of the equation.

The other part was that at this same time, my profile as an “expert” in the bootstrapping space continued to grow.

The fact that my name became synonymous with Tamboo started to wear on me.

Here was this thing that I had started to grow in a very strategic way that all of a sudden is getting all of this attention, but none of that traffic or attention are “converting” properly.

And that was fucking with me.

Now, it wasn’t that Tamboo wasn’t growing or that it wasn’t “working”. It was just that it wasn’t growing or working the way that I thought it should now that it had all of this “free marketing” getting thrown at it.

And while all this is going on, preorders for the book keep pouring in, my followers keep growing, and more and more people keep discovering The Epic Guide and for some reason or another prop me up as some kind of a startup hero to be revered and looked up to.

This internal dichotomy started to mess with me.

Here I was, trying to figure out how to get this thing to convert all of this newfound traffic and attention into something meaningful, while at the same time everyone thinks that I’m some sort of magical startup hero who has all the answers.

But I’m not a hero.

I’m just a dude.

I do not have nor have I ever been imbued with any kind of startup superpowers.

But that didn’t seem to stop people from thinking otherwise.

My articles continued to get more and more popular. My inbox got more and more emails. And I continued to get more and more preorders for the book.

It’s around this point in time that I started to feel like I can’t fuck up for fear of some kind of a fallout.

The fucked up “growth” that Tamboo was experiencing and the fucked up live demo and free trial fiascos that were causing me to want to rip my hair out couldn’t ever be discussed because… what would people think?

So the pressure got to me a bit and I kind of lost it.

I was spending an inordinate amount of time trying to figure out how to get my conversion and retention numbers from these people to work and I wasn’t getting much of anything else done.

Plus, I felt that maybe free trials, as standard as they are for other SaaS apps, might not be the way to go with Tamboo. You see, free trials mostly exist to 1) get people in the door and 2) give people time to get setup in a new app and to achieve some goal/get some outcome before being required to pay as a way to reduce early friction (and get them hooked).

With Tamboo, people got value out of the gate. And I had a sneaking suspicion that people were using the trial, getting that upfront value, and then just going their merry way.

So I killed the live demo and ripped out free trials and forced everyone to “pay to play” —aka credit card and payment up front.

That was probably a little hasty, but it felt so fucking good.

The minute those changes went live, my inbox got quiet. Real quiet.

I wasn’t getting notifications about new “leads” I had to track down. I wasn’t getting error reports about shit breaking in a demo or getting support requests from people in a free trial complaining about something not working right (or at least not how they expected).

If you wanted my attention, you’d at least be a paying customer.

It was bliss.

It was at that time that I decided to switch gears and put some focus into this book, which was continuing to get steam and traction and weighing on me more and more each day.

I spent most of the rest of June focused on the book now that I could stop worrying about demos and trials and tire kickers.


Instead of stressing about Tamboo in July, I shifted most of my focus to the book (which I in turn wound up stressing about).

Writing the first pass of the first part of the book took much longer and required much more effort than I had anticipated.

It took me a little while to “find my groove”. Writing a book is very different from writing a bunch of blog posts. (Anyone who’s made an attempt at one will know what I’m talking about.)

I wound up writing something like 300 pages in a marathon multi-week writing session.

Then I threw it all away and started over from scratch.

The second round, I wrote something like 200 pages and wound up throwing 75 pages or so to the cutting room floor, leaving me with about 125 pages give or take.

Editing took far more time than I would have ever imagined.

I think that I went through three or four editing passes on the first part before I finally thought it was at a point where I felt comfortable releasing it.

I was a little nervous releasing such a monster (it was the first release, clocking in at over 100 pages), but at the same time I had reviewed and edited it enough that I was pretty confident in what I had put together.

Still, hitting “send” on that email list was honestly a little scary.

But it turns out people loved it and I got a lot of positive feedback and encouragement.



I really enjoyed working on writing the first part of the book. I had dreaded the effort that would be involved, but once I got into it, I really thoroughly enjoyed it. Shipping it felt even more awesome (I love shipping — there is no feeling quite like it).

But that whole time, I was stressing about Tamboo and all the things I wasn’t doing there.

Ever since I had killed off the live demo and the free trials, signups had plunged.

This was to be expected, but I knew that in order to maximize those pay-up-front conversions, that I would need to do a better job of showcasing and explaining Tamboo on the marketing site.

Up until then, I could afford to have less on the marketing site because the free trial kind of offset any kind of risk for people to try it out.

Not having any kind of trial anymore, I needed to really up the potency of my marketing site to convince people to fork over their credit card for something they couldn’t try out first.

So I did just that and completely overhauled the marketing site and pricing structure (again).

Like I had mentioned before, I thought that offering pricing around the number of websites that someone would want to use Tamboo on would be a logical way to segment tiers, but it just didn’t seem to be resonating the way that I thought it would. So I switched back to usage-based pricing, but I structured the plans around customer segments to make it scream “this is for me” to them. So I now had plans for “Personal”, “Startup”, “Business”, and “Agency” to target those different classes of users, which would hopefully help overcome any kind of confusion about recording limits.

Daddy’s gotta go to work.

I also did some much needed marketing and promotion for Tamboo, but in hindsight, I was doing it in the wrong places again (more on that later).

At the end of August, I decided to bite the bullet and start the process of launching a podcast, which is something I’ve been wanting to do for a long time (sort of like writing the book). To gauge intereset, I created a landing page for SaaS In Gear and started promoting it, following my tried and tested method with the goal of getting 100 signups.


Then September hit, and I had a serious meltdown.

Shit was starting to wear on me.


It’s around this time that I started to feel like the market for Tamboo had somehow moved under me, and that I had missed a huge opportunity by having my focus and attention diverted by this whole “startup culture” thing I had somehow found myself wrapped up in.

Somehow, all of the effort that I had exerted to date caught up with me in one massive tidal wave of despair.

All of the late nights, all of the weekends, all of the emails, all of the seemingly endless refactoring and tweaking, all of the marketing site updates, all of the never ending support requests, all of the writing, all of the forums, all of the Slack groups, all of the shitty conversion rates, all of the atrocious retention numbers, all of the, all of the, all of the… everything.

It just hit me.

Very much like a ton of bricks.

I shut down.

I became despondent.

I started to feel like I had back in 2016 when everything fell out from under me.

Sure, this was very different from then. After all, my revenue was going up instead of down, and I was still moving in the “right” direction — just not in the way that I wanted to, and not in the way that I thought that I should.

But I still had this feeling that what I was doing wasn’t somehow right.

That I was screwing something up by not being as focused as I should on the things that I knew I should and that in the process, I was missing out on something much bigger.

And that I somehow might have “missed the boat” by the time I realized it.

It was at this time that I started to “feel” that things had somehow changed over the past few months.

I’d completely cut off trials, so I knew things would be much slower and less action-packed, but I felt that there was something else going on — something that was out of my control.

I didn’t have anything to support my suspicions, but I started to feel that session replay tools had become commoditized by my competitors — and that they had somehow turned this whole market into a race to the bottom.

This suspicion came from the observation that pretty much every one of my competitors were now engaged in a freemium play — offering completely free tiers for their products. And seeing a lot of people starting to tout that as a “benefit” — “You can use it for free!”

As a bootstrapper, you don’t want to get into a freemium fight if you can avoid it.

Freemium — especially in a resource intense business like session recordings — can be very expensive.

Based on what I knew, I’d come to the conclusion that the largest of my competitors had used their freemium play as a way to basically corner the market and juice their SEO.

In the process, they were forcing everyone else in the market to follow suite if they wanted to stay in the game.

The vast majority of their “customers” don’t pay for their service, but since they had a nice little war chest to burn, and since it helped them maintain their market dominance, they seemed to be fine with that. They were still making bank from the other side of the freemium play, and so it seemed to be working out masterfully for them.

They were able to keep low-cost competitors from “stealing away” at the lower end of their customer base by offering a free tier, and they were able to maintain their higher price point by being “number one”.

I didn’t know if this was a game that I wanted to play anymore.

I was beat down and worn out and I just didn’t know if I had it in me to fight this fight anymore.

I gave myself permission to crash.

And so I did.

A few days later, I picked myself back up.

I knew that feeling sorry for myself wasn’t going to fix anything.

The only thing that would fix anything would be to get back up and face these things head on.

So that’s what I did.

My name… is Neo.

I wrote down all of the shit that was getting to me.

And then I asked myself what I could do about each of the things I had written down.

If I couldn’t do anything about it, I told myself to suck it up and crossed it off the list.

If I could do something about it, I forced myself to figure out what I could do — even if it wasn’t a guaranteed “fix”. (Any action is better than no action.)

This exercise helped, but it didn’t take the emotional drain I was feeling away. It just gave me a course of action.

And so I went to work.

I continued to promote the podcast launch list.

I tackled some nasty support issues for some new customers that took a lot of time and effort.

I worked on Part 2 of The Epic Guide Book.

I made some performance and stability improvements.

I tweaked some UI and UX things.

I started working on adding a custom funnel feature to Tamboo.

All in all, I came back swinging in September, even though I still felt like shit the whole time.

It was around this time that I started feeling like I just wanted to shut down and do me and not worry about anyone else. So I pulled back on Twitter, email, Slack, forums, etc. This was the start of me going “inside” and just wanting to insulate myself from everything.


In October, I finished and rolled out the custom funnel feature for Tamboo, as well as completely gutted the heatmap engine again (this is the third time if you lost track) and added support for mouse movement heatmaps.

And of course, it’s pretty much useless to add new features and not tell anyone about them, so I made some marketing site updates and did some promoting to showcase the new funnels and heatmaps.

I even gave one more last-ditch effort to try to convert some of my Medium traffic by creating a special offer to get a copy of my book when people from Medium signed up for Tamboo (I still couldn’t let that go for some reason).

I spent (a lot) of time finishing up the second part of The Epic Guide Book, including spending what I would consider an obscene amount of time working on illustrations for it. Shipping the second part and getting some of that built-up pressure off my plate felt good, kind of like coming home and just crashing on your couch after a long day at work.

And if all of that wasn’t enough, I also wrote and published Part 5 of The Epic Guide Medium series, which was (embarrassingly) the first update to the series in months.

I was worn down, and not feeling very social, but I was at least still moving.


All of that caught up with me in November.

I still did stuff, but it was getting harder and harder to get back up.

I got swamped pretty early on with some more intense support issues from new customers (this shit is hard, if you haven’t caught on yet).

I spent about a week fucking with heatmaps again (fourth rewrite in the year).

I marketed.

I started Tamboo Academy.

I started a prototype of a website chat feature.

I ran (keep in mind, I’m still training for an ultramarathon during all of this).

And I finally caved and brought back trials.

Signups were too low for my taste with the “pay up front” approach, so I compromised and decided to do credit card upfront trials (which have worked out better).

The whole time, I just felt down and didn’t really want to talk to anyone about anything.

I was really starting to feel this whole “split brain” life I was living.

On one hand, I have this great application that I spent a shit ton of time on that I feel has a lot of potential, but that I don’t feel I’m focusing on in the right way, and that could have more outsized results if I’d just go all-in on it. It isn’t easy to work with (there are days I absolutely hate working on this thing), and it seems to be getting harder to market it. There are things that I would love to do with it, but I just can’t bring myself to do those things unless I can get my conversion and retention rates where I want them to be. I’ve been half tempted to just put the thing on autopilot, be happy with the income it generates, and shift my focus to something else. It‘s not something that I necessarily enjoy anymore. There are times when I feel like I just can’t turn it into what I had originally wanted it to be anymore, and that I just haven’t been properly focused on putting my efforts towards the right markets for it.

On the other hand, I’ve built up this “startup personality” thing somehow, and I really enjoy writing and helping people get and see traction with their projects. (At least when I’m not emotionally burned out by everything.) I get honest enjoyment from helping people go from “I’m stuck and frustrated” to “I’m making $1,000 MRR!”. I feel honest pride and admiration for them, and it makes me feel like I have a purpose bigger than just eeking out another tenth of a conversion rate percent on my website.

But I was starting to see that the two are incompatible and are actually at odds with each other.

Like I’ve mentioned before, Tamboo had (and continues to get) a lot of attention from my Medium articles and all of the sites that link back to it because of my “startup status”.

But hardly any of that has resulted in any kind of actual, tangible business results for Tamboo.

The vast majority of the people who have paid for Tamboo did not come from any of those efforts or traffic.

By my calculations, roughly 3% of all paying Tamboo customers can be directly attributed to those sources.


And yet I’ve wound up spending a shit ton of my time contributing to that community since last year.

(And sure, I’m not going to lie — I’ve tried converting some of that traffic and attention, but it just doesn’t seem to want to be converted.)

But doing both when neither benefits the other, and when they both push and pull at me in very different ways that leave me exhausted, feeling like I’m failing at my goals for either, and make me feel like working on one over the other is causing me to choose which one I want to see fall behind even more?

I just don’t know.


By December, I’m feeling overwhelmed and ready to just curl into a ball and wait it out until January.

It started off okay enough.

I did some more marketing. I did some more customer onboarding.

But things kind of fell off the rails early on.

Maybe it was the fallout that hit the session replay market from a widely publicized “study” that got covered in near every major tech publication. (A lot of us saw a major drop in subscribers as a result of that. I even had a few people start leaving me “love notes” on Tamboo’s website. Definitely “motivating” stuff.)

Or maybe it was the one customer that I had spent a few days helping to get onboarded (due to some issues with the way they had coded their website) that decided to just cancel on me that sort of pushed me over the edge.

Any one of these might have been the straw that broke the camel’s back, but it was a long time coming.

Despite all of the effort I put into my training this year, logging a shit ton of runs and miles, doing all kinds of interval and hill training exercises, including building up to half-marathons on the weekend, being super careful with everything I was eating and doing, and starting to get pretty damned ripped, I stopped running and put on a fair amount of “winter weight”.

I basically stalled on moving forward with my podcast, because I just couldn’t bring myself to talk into a microphone without sounding despondent and burned out.

I haven’t touched my book since releasing the last part in October, mostly because I just can’t bring myself to losing another month of progress on my business.

I haven’t been very “social” on the internet or otherwise. I just don’t have anything really positive to say right now, and I just kind of want to be left alone with my own thoughts.

And then throw in getting sick as a dog this past week, and that’s pretty much a recipe to just step back and want to admit defeat.

A lot of people have told me that they like me and my writing because I don’t bullshit.

Well, here you go.

No bullshit.

I’m burned out. I’m torn. And I don’t know how to go forward.

Just to get away from some of this, I started working on an open source project just to have something “exciting” to play with. So when you might think “Wow, he’s even doing an open source SaaS-in-a-box!”, it’s really just a distraction for me from this other shit.

Despite all of my experience building software-based businesses, I’ve never built a startup with ambitions like Tamboo before, and I’ve never had an audience or a following either.

So I’m not sure how to go about “this”.

Because I’ve never done “this” before.

Contrary to what you might think, I don’t have all the answers.

And I’m tired of feeling like I have to.

So I guess I have some decisions I have to make this upcoming year.

Don’t worry — I’m not going to leave anyone high and dry.

I’m still going to finish this book, and I’m still going to keep Tamboo chugging along.

But do I continue to live this split-brain existence?

Do I choose one over the other?

Or do I somehow make them “align”?

Right now, I don’t know.

But I do know that whatever choice I make will shape where I go this coming year, just like the choices I made earlier last year led me to where I am today.

Do I lick my wounds and walk away, choosing one over the other?

Or do I find a way to swing back at both?

Happy Holidays.

And Happy New Year.