Learning to be a CEO

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From freelancing to running a 20-employees business in 20 months

“Bumpy track” — I took this picture in Battambang, Cambodia in 2017 during a life-changing 4-month trip throughout Oceania and South-east Asia with my wife. In case you’re wondering, no it’s not an optical illusion and yes that tracks is used by wagons!I have no idea how to do my job.

OK, that may be slightly exaggerated but while it’s not my first entrepreneurial venture, it’s the most successful one — by a landslide.

As I reflect on the past 2 years since I decided to quit my last job, here are a few lessons I learned along the journey of becoming the CEO of a bootstrapped-remote-first consulting company with over 20 employees distributed across 3 continents.

The resignation before the great resignation 🔚

My decision to quit my job as a Data Product Manager mid-2019 came from accumulated frustration made up of contempt for internal politics and a feeling of having good ideas that were not considered but mostly, I was missing being the master of my own fate.

This frustration actually started to have an impact on my health as I started to have regular panic attacks.

But to do what? Start another job? No. I wanted the freelancing life. The perfect plan on paper: work for 6 months, travel & write for 6 months.

Freelancing it is. The question was: what was I good at? All my life, I’ve been the “data person” in my various jobs in Finance, Marketing, Operations, Sales and Product. Need an Excel Macro? A dashboard on Tableau? Rolling out Looker? No worries. I like doing that sort of things and I’m pretty good at them too (or used to be anyway).

And so, I sought contract work around the modern data stack under the name “Montreal Analytics” (I live in Montreal, Canada, in case that was not clear).

After a couple of short gigs, suddenly came larger contracts over a few months and I suddenly found myself billing over 50h/week (and if you’re currently freelancing, you know it means that you’re effectively working 60h — at least).

Lessons learned & advice

Make sure your significant other is onboard and will support you.If your skills are a hot commodity, you can get some gigs pretty easily.Seek work from your former employers (ideally, if you have a good relationship with them!).It may take a few weeks/months before you get that first real contract that puts food on the table. Keep pushing!Be flexible in your service offering (rate, methodology, projects, etc.) at first until you find the right setup.Use a tool like Wise (that’s my referral link) to receive international payments.

At the crossroads: scale down 📉 or up 📈

When I started, I was not expecting to find so much work so fast. I was doing pretty good money-wise and the market was hot for what I was doing. But working 60+ hours/week for others was starting to bring me back to my frustrations.

And so, I contemplated the two paths that lie before me:

Scale up: Make this an actual business, incorporate, build partnerships, find clients and hire employees: work more, for less money with the potential of a much larger payout.Scale down: Only take 30h/week worth of contracts: work less, accept that it’s fine to leave money on the table with the trade off of freeing time for other things.

I knew that building the discipline to say no would be hard for me. Furthermore, I accepted the fact that freelancing was maybe not my favourite way of working as I’m more of a builder.

And so I chose the path to building a business instead of an activity.

Lessons learned & advice

Make sure your significant other is onboard and will support you (bis).While seeking larger contracts, you can leverage other freelancers but NEVER accept work that you don’t feel comfortable taking over yourself, because sh*t will hit the fan and you’ll be the one left to pick up the pieces.After a few contracts/months, do some introspection: is freelancing the right thing for you (and not just financially)?

Bootstrapping a consulting firm 🛠

So, I had a business name that I was already using which I transferred into an incorporated company of the same name.

At first, I decided to partner with a friend, equity against work for a few months until we’d have built enough cashflow for salaries but after a couple of months we decided to part ways, it was not working.

Now, I needed more contracts to be able to put some cash in the bank and make sure I could hire my first employee:

I leveraged my relationships with folks at Looker (now part of Google) to become a registered partner and they started to send clients my way which helped drastically to get things started.I started a blog focused on tutorials and guides in order to build credibility and drive traffic to the website.I sought a long-term contract intended for a potential first hire

All that worked really well. Despite Covid hitting us a couple of months only after starting the company, we did a very solid first year, reaching 4 employees in December 2020.

Lessons learned & advice

Make sure your significant other is onboard and will support you (ter).Don’t get in business with friends, unless you’ve worked with them extensively beforehandPartnerships with tech companies were key to our success. Focus on 2/3 of them, build the trust and the relationships with the sales team.Good content that brings value to your readers without expecting anything in return (i.e. their email) is VERY valuable.Find the best of the best for your first hires as it will set the bar for future employees. It’s going to be hard to convince them to join, so make sure you pay market salaries and be open to giving away some equity (under vesting).Don’t underestimate the value of a good lawyer for your initial legal setup. It might save you a lot of money and headaches down the road.If you can manage without an office, do without an office! The cost savings are huge. Put that money into salaries and perks, it’ll make it easier to recruit!

Learning to be a CEO 🚀

The first six months of 2021 have shown quite a nice growth, we hired 5 people, effectively doubling the team (9 teammates).

At that time I was still doing a lot of billable time while running the company which means that I always worked over 60h a week and often over 70h. Definitely not sustainable.

Change was most needed:

We created some structure in the organization. My two first employees became leads and they took over some of my responsibilities.We decided to change the strategy of the company from “normal” growth to hyper growth in order to capture more of the market faster.As CEO, I was to focus more “on the business” as opposed to working “in the business”One of our employee got promoted to “Chief of Staff” in order to make operations & special projects move faster.We hired someone to run human resources as it became clear it was a full time job.Because hiring was really strategic, we tripled our effort (sourcing, interviews, employers brand, etc.) and spendings.

All that led to a spectacular Q3 2021 with 13 new hires, bringing the company to 22 employees, located in various cities of Canada, Brazil and Portugal.

The key realization for me this year, as we scaled, was to realize that I could not realistically be aware of everything that was happening within the company or even on clients projects. Even if I drastically reduced my billable time (without stopping because believe it or not, I actually like to code!), that was too much brain time. So, I learned to trust & delegate, which was hard for someone like me that is a bit of a control freak.

I decided to focus on a few things:

Fostering a culture that brings the best in peopleSupporting the team wherever and however I canFiguring out what’s next for the company (marketing, partnerships, organizational structure, work methodologies, tech practices, etc.)

Lessons learned & advice

Make sure your significant other is onboard and will support you (quater).Your growth needs to be self-sustainable: build a forecast for your hiring plan, revenue, costs & cashflow. Check every month where your actuals stand compared to your plan and readjust if need be.Making payroll is crucial so ideally, you want a runway of 6 months without revenue.When there is a doubt, there is no doubt: don’t agonize on difficult decisions and trust your guts more often than not.Learn to trust and delegate.Groom and enable teammates that you want to see grow in the company.

We’re now almost in October 2021, I’m about to turn 36 and hopefully run a company of 35 employees at the end of the year. It’s been the best 2 years of my life so far. A lot of work, a lot of stress but also a lot of joy, a lot of laughs and definitely a lot of learnings.

And you know what’s even better?

My significant other is still supporting me.

About Montreal Analytics

Proudly bearing the city name where it was born, Montreal Analytics is a boutique consulting firm that leverages the power of various cloud technologies to further the democratization of data within companies. We help companies build up their Analytics organization through technology, technical, and business training as well as recruiting.We are trusted consulting partners of Google, Looker, dbt, Snowflake and Fivetran

Let’s chat 👉🏼 https://montrealanalytics.com

Learning to be a CEO was originally published in The Startup on Medium, where people are continuing the conversation by highlighting and responding to this story.

The Startup – Medium

freelancing, startup-lessons, entrepreneurship, business-development, analytics

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