Building a successful company is fucking hard.
11 min read

Building a successful company is fucking hard.

Navigating my first 10 years of full-time entrepreneurship from dozens in failures to millions in revenue.
Building a successful company is fucking hard.

This post is for everyone who is trying to start a company right now.

The headlines make it seem easy.

20 year old kids raising millions of dollars to build the next Snapchat. Smug digital nomads posted up on a beach in Thailand making $75k/month. That lifestyle design dude who made $200k selling a Twitter course this year.

Unfortunately, it's not that simple.  

It's fucking hard.

At least it was for me.

I wanted to be a millionaire by 30. I was broke at 25.

I launched dozens of products, navigated through the minefield, and came out of it with business that exceeded all my expectations - millions in annual recurring revenue.

Here's the true story.

Year 0 (inspiration)

About 10 years ago I unofficially graduated university.

I had the credits to finish early, but stuck around to take one last class.

New Venture Design paired up business and engineering students to build a company.

That class changed my life.

My accounting major put me in the "useless business guy" category, so I consciously recruited the only two software engineers in the class.

The project we dreamed up was a daylighting system for commercial office buildings we called Luminex.

Essentially, reflective venetian blinds that tracked the sun and automatically reflected light into the ceiling - so you can work at your computer with natural light and no glare.

Rendering of the project

Still one of my best ideas.

Instead of testing it in the market, the primary objective was to compete in business plan competitions. Which just means pitching to students and professors. It had nothing to do with building a successful business.

We won three competitions -  taking home $15,000 in prize money.

It was a great way to cap off my university career.

We graduated in May 2011, and decided to pursue the idea full-time.

Year 1 (optimism)

One school never paid out their $5000 prize (thanks for nothing, UNBC!).

So with $10,000 in winnings to our name, we were ready to take on the world.

Along with our business plan competition spoils, I personally had $8,000 saved.

I never considered getting a real job.

I didn't jive with the dogma business school pushed on its impressionable young students. Recruiting events with a bunch of 20 year olds putting on suits to impress 23 year olds in suits for the privilege of making $40k/year working 80 hours a week.  The weird reverence for McKinsey and KPMG.

I had some experience making my own money - running a window cleaning company that grossed $45k one summer - and once you've charged your friends out for $30/hr and paid them $15, it's hard to imagine working for anyone else.

The three of us were ready to build a hardware company. With $10,000.

A month after jumping into the abyss, we quickly realized we had no idea what we were doing and no money to do it with. The extent of our market validation was a few random people telling us our idea was good, and a prototype with some really decent software on it.

It took 3 months to realize it was never going to work. One engineer quit.

We were down to a partnership with no plan, no direction, no strategy, and no money. Yet, I still had a weird optimism that I'd figure it out.

I made $7,000 this year.

Year 2  (survival)

At the time, I was living in an amazing downtown apartment with two friends.

We squeezed 3 of us into a 2 bedroom + den apartment, on a grandfathered $2200/mo lease. My share was $800.

My friends all had real jobs at this point, but it never crossed my mind to get one.

I didn't want to move back home. I didn't want to get a job. I didn't even know what a job looked like (still don't!).

My only goals were to make that rent payment, drink a few beers, try to meet women, and eat. My business partner and I turned to what we knew.


More specifically, web development on Craigslist.

We started building average Wordpress websites for small businesses, averaging $1000 to $4000 per month in sales from posting ads on Craigslist.

To supplement that kinglike income, we also started blogging on Seeking Alpha - writing stock investment advice for $80-$300 per article.

Stock Picks, Stock Market Investing

I had never bought a stock, and here I was - writing about Apple's future.

I should have bought Apple stock.

We shipped dozens of projects.

A website that paired up students and businesses, an events listing website, a Wordpress theme directory, a platform that helped companies pre-test job applicants skills, and many other forgotten ones.

The worst one was probably office composting.

Urban Dirt picked up your organic waste (in a rented Zipcar, as I didn't own a vehicle), and dropped it off at a composting facility for $30/week.

We got 10 customers for that business, and nearly landed the contract for Rogers Arena (Home of the Canucks) through a cold call. Hundreds of dollars of revenue wasn't enough, so we decided to make a huge bet on making our own fertilizer out of used coffee grounds from Starbucks.

This image gives me shivers.

We spent weeks drying coffee grounds on homemade racks and packaging it in paper bags to sell at farmers markets. We sold $40 worth.

I rented my room out on AirBnB on the weekends and slept on my couch to make ends meet. I don't know what the fuck I was thinking.

I made $30,000 in 2012.

Year 3 (momentum)

To summarize - two years into my entrepreneurship journey I was somewhat scraping by building crappy websites for random businesses, blogging about stocks that I wasn't invested in, and slanging fertilizer.



Yet, not ready to quit.

I don't remember the genesis, but one project we ended up building was an applicant tracking system. I'm sure I've told the story about how we wanted to hire for our web design agency and needed a way to track applicants so we built this software to solve our own problem.

That's a lie - our agency never hired anyone. We probably built that software because I saw it somewhere and it looked like something we could build.

Anyways, we built an applicant tracking system (it worked!) and I hustled my ass off to sign up customers.

A few companies (thanks Charlyne, Heidi, and Gord) believed in us enough to pay us a little bit of money for it. From there, we had a few more ideas around the recruitment space - again, likely borrowed. One idea was a really cool tool that helped asynchronously test out job applicants skills before they got hired.

Similar to Codility, but for everyone.

We couldn't get customers. People just wanted an applicant tracking system.

We tried to make that applicant tracking system sexier, by allowing companies to add pictures/videos of their companies to their job postings. Like Unbounce for your job postings. No one wanted it.

We got desperate.

To promote our product, we decided to host an online job fair. We dreamed up the idea for an online event where candidates could visit company "booths," chat with recruiters, and drop their resume.

We set a 6 week deadline to launch and promote it.

I hit the phones hard, and signed up 40 companies. My cofounder built the software. We got press in some of the countries' biggest publications. Thousands of candidates pre-registered for the event.

We went live on 2pm on Monday, July 23rd.

Our servers crashed.

I punched a wall.

Matt (who we were sharing an office space with) got our servers back up, and the site held together for a few hours. Overall it was a very average experience, but enough to get us on the radar of Growlab - Vancouver's version of YCombinator.

Growlab was a group of experienced entrepreneurs and mentors who invested $20,000 in startups with the goal of helping them raise more money. That online job fair got us on their radar, and we got into the program.

One minor issue - we had no idea what the fuck we were doing.

At this point we had 4 products in the market with a handful of users.

An applicant tracking system (~1k MRR)

Asyncronous skills testing (alpha product)

Unbounce for job postings (~50 users)

An online job fair platform (1 event)

We had no vision, and no direction.

Growlab invested $20,000. This was the most money I'd seen in a bank account in 3 years. If we met minimum criteria, the Business Development Bank of Canada would invest another $150,000 into the company after 3 months.  

We decided to focus on KarmaHire - Unbounce for job postings.

It hurts my brain to think about trying to get that thing off the ground back then.

I tried everything.

Automatically creating job postings for companies on Indeed, and then sending them the postings. Cold calling from 7am to 8pm (on the damn PHONE).

I was under the gun, and nothing was working.

My stress levels were through the roof. I was telling a story every week to our investors that had a hint of truth to it, and failing to make that reality come true.

Unnamed mentor gave me some of the worst fucking advice I've gotten.

"Never let the truth get in the way of a good story."

I've always had a guilty conscience, and while by the letter of the law I was telling the truth - it hurt my soul to extrapolate tiny data points into a broad narrative.

My stress levels peaked one Wednesday in May.

I got to the office at 7am, ready to start cold-calling. I reached into my backpack and realized I forgot my laptop at home.

I cracked.

I stumbled out of the office in a daze, walking home with no regard for red lights or traffic laws. I nearly got hit by a car. Twice.

I was completely checked out. The only thing that brought me back to sanity was the fact that my Grandma picked up the phone when I called her. We talked about nothing of substance, but she told me she loved me.

I made it home and slept for 6 hours. And went back to work the next day.

We survived Growlab, and impressed the BDC enough to raise that $150,000.

It may have been the haircut more than the product.

The techiest of tech bros.

A lifeline, and a hint of validation.

Despite its challenges, Growlab accelerated my learning 10x. I learned how to craft a narrative, to ship product faster, to raise money, and to get press. I met incredible founders, investors, and mentors. I wish I had enjoyed it more.

At this point I'm four years into this shit.

We raised that $150,000 on a story that felt real at the time, but had no substance.

Our investors lost interest. We were on our own again.

The only thing we had that had generated real revenue was this online job fair platform. We switched focus. I started selling again.

I sold an $80,000 contract to the City of Prince George. A $40,00 contract to a mining company to do virtual town halls (they never used it, but did pay us). We signed up Dartmouth College, ran our own college online job fairs, and squeezed out as much revenue as we could.

I was working the proverbial 12 hour days. We were cold emailing, cold-calling, and hustling our asses off to make this thing work.

It wasn't going to work. At least not at the scale it needed to. The online job fair platform never picked up any natural momentum. It never hit escape velocity, and was a failure as a funded business.

If we had continued on that path no doubt we could have built a decent business, but not one that returned capital. Hell, if we stayed alive until 2020 maybe we would have become

We did not.

I took home $35,000 in 2013.

Year 4 (revival)

The new year rolled around and I was ready to quit.

We were working our asses off to squeeze water from a stone.

3 years felt like a lifetime.

We had launched nearly a dozen products, made barely $140,000 in revenue, raised $200,000, and was totally burnt out.

I was ready to throw in the towel and get a job.  

It was time to say goodbye to the entrepreneurial journey, for now. By all accounts, I had failed pretty miserably.

My friend had just raised a Series A for his health tech company in Silicon Valley, and I almost took a job with him. If I had any confidence that I'd bring any value to the company, I probably would have taken it.

Instead, I tried to sell the pieces of our current company. We had $50,00 left in the bank, 2 products in the market, and negligible recurring revenue. No value.

In attempting to sell the company, I met the founders of an enterprise recruitment software company with ~100 employees. I wanted to sell to them.

I cold emailed their CEO, and got the meeting. It went well.

I never heard back.

I followed up 8 times. Turns out they had acquired a website a few years ago that was sitting on the shelf - VisualCV. It had raised money in 2004, flatlined, and died. But it had a nice domain name.

Long story short - myself and my partner formed a new company with the partners at that company, acquired the domain, and tried to make it a business.

I had a three month plan.

If this worked, it seemed slightly better than getting a job.

We got to work. Rebuilt the entire product and marketing site. Relaunched in May 2014. In August we rolled out pricing.

We made $5000 our first month.

In 3 months, we took the site from death's door to ramen profitability.

In October, we launched on Product Hunt. Things picked up from there.

I made $60,000 in 2014.

Year 5 (growth)

Within a year we were at $1m ARR with two employees.


I started to breathe a little easier.

The team grew slowly while revenue grew quickly. I moved to Argentina for three months, and managed the team from there.

My personal income grew 10x.

Externally, I was living the remote work dream - profitable business, small team, working from anywhere. Not a whole lot changed internally.

Every day I was stressed.

Sometimes the stress was warranted - DDOS attacks, major bugs, and Google Algorithm changes.

Most of the time it was the lack of stress that caused the stress.

Instead of embracing the freedom, dreaming bigger, and enjoying the ride - I lived constantly with the fear that it would all fall apart. I spent days and days locked in analysis paralysis, trying to figure out what to work on.

I liked when there were fires to put out  - it made me feel useful.

That underlying feeling of "is this it?" gnawed at me. I filled the void with travel, alcohol, sports, and the usual distractions.

Despite constantly wrestling with my demons, I got a few things right.

We doubled down on what worked. Scaled our marketing. Built a solid brand.

In 5 years I grew the company to over 4 million users and $2m+ ARR with a fully-remote team. Last February, I replaced myself as CEO.

I'm still a proud shareholder and board member, and excited for what's ahead.

I'm grateful to have navigated my way through the minefield, and come out relatively unscathed.

In a decade, I built something significant.  I've helped millions of people get jobs. I've created wealth for my family. I've met lifelong friends, and seen them build billion-dollar companies with hundreds of employees.

I've learned a lot.

If anything, I've lifted the veil enough to understand that the world might just bend to your will if you work at it long enough.

Success is a result of hard work, talent, and luck.

You can only get lucky if you're in the game.

If you think this is what you might want to do with your life, I suggest you get in the damn game.

Enjoying these posts? Subscribe for more

Subscribe now
Already have an account? Sign in
You've successfully subscribed to Mistakes of Ambition.
Success! Your account is fully activated, you now have access to all content.
Success! Your billing info is updated.