Field Notes / Consulting, kids, and kidney stones: My first three months as a solopreneur

Consulting, kids, and kidney stones: My first three months as a solopreneur

In this edition of Field Notes, I share the ups and downs from my first few months as a solopreneur.

Let me start by saying the kidney stones weren’t that bad. Well, they were, but only for a day. We’ll get to that later.

The rest of the last three months has been incredible.

And the best part by a billion miles? I became a dad again!!

Everybody, say hi to Desmond 👋

Desmond Norm Hennig was born September 25, 2022. He also goes by Des, Desi, and Mondo, although nicknames are sure to expand. Mama is doing great and Nana and Pop Pop are here to help, so all is well.

There’s nothing like a new baby to put things into perspective, huh?

It’s certainly validated my choice to quit my job and be my own boss. Having the ability to choose my own hours, unplug when I want, and only work on the things that — in Marie Kondo terms — spark joy is priceless.

That said, I’m still in the honeymoon phase, y’know?

Yes, going solo feels like the best decision ever.

And yes, I think I should have done it sooner.

And yes, I love that I don’t have to be an adult babysitter or sit through endless meetings or report to someone else anymore.

But let’s not kid ourselves. I’m three months in. I have apples in my fridge older than my entrepreneurship career, so let’s maintain some perspective.

The following is an update I plan on giving quarterly, similar to how others write imaginary “investor updates” to keep people in the loop and digest their learnings. Desi says we’re OK to proceed with the update, so lessgo.

Financial update: How much have I made?

Good news: I’m not broke yet! Yippee ki yay, mother#$@%!s.

In fact, I’m happy to report that I’m pacing above the targets I originally shared. Unlike many people who build in public, however, I’ve decided not to disclose specific amounts for personal reasons. “Like cornrows and sleeve tattoos, I’m glad other people do it but it’s not for me.” —Sam Parr

That said, I will share a breakdown of where the revenue came from because it’s one of my goals to adjust the split of sources over time.

Here’s how my earnings in the last three months break down…

Here are some observations from each of the four categories.

1. Analyst projects brought home the most bacon. I’ve been working with a company called SelectHub to launch their analyst program and it’s going well. We’ve developed content together, and I’ve starred in several of their YouTube videos — see example below. Enormous potential here. This took half my time this quarter, but now we have a well-oiled production engine in place and a dedicated sales team to help scale.

Example of analyst content done with SelectHub. We’ve completed two projects and plan to scale.

Example of analyst content done with SelectHub. We’ve completed two projects and plan to scale.

2. Consulting was crazy busy, then slow, now crazy again. I made $30-40k in consulting in June and July but almost nothing in August. Then, as soon as September hit, my calendar filled up again. I’m guessing it’s because the hedge fund managers I typically work with were out “summering” and are now back. We’ll see. My Hamptons invite must’ve gotten lost in the mail.

3. Affiliate marketing performed worse than expected. My affiliate income has been trending downwards since Jan, likely due to the recession and reduced demand for the companies I work with. Despite launching new content, closes suck. I’ll consider it troubling if there’s no rebound in 3 months. For now, I’m focused on content optimization and testing offers.

4. Advertising started to take off. Notice that teeny 2.6% slice of the pie? That’s me starting to sell ads on my personal site. Love it because it’s recurring rev and the work is already done. Aiming to triple next quarter.

What have I learned so far?

Here’s what I’ve learned so far in no particular order.

>> Speed matters. At least 50% of my consulting revenue comes from same-week bookings. If I don’t offer availability within a few days, clients will go cold. When someone asks to connect, reply in minutes not hours.

>> Cold emailing is a super power. Marketers hate cold email but it’s my most affordable acquisition channel. Pro tips: cut ALL bullshit and show personality. Also, try the subject line “Taking a punt”. Works wonders.

>> Teleconferencing is alive and well. The best part about consulting with hedge funds and management firms is that they love audio-only calls, so you don’t have to worry about looking good.

>> Freelancers trump employees. So much time is wasted in the corporate world trying to figure out how to compromise with coworkers and give out compliment sandwiches so working relationships don’t go sour. Projects suffer and take waaay too long. I much prefer having an A-Team of contractors to whom I can give marching orders, deliver blunt feedback, and assemble / disassemble when needed, similar to the Hollywood model.

>> Charging in USD is great. Despite its best attempts, the United States hasn’t imploded yet. By charging in USD, which no one blinks at, I’ve made around $30k extra thanks to exchange rates alone. Neat-o.

>> Tweeting every day is hard. I told myself to do it because that’s how you build an audience, but the way I’ve been going about it is a waste of time and I need to rethink my approach to better fit my goals.

>> Auto-transcriptions in Adobe Premiere are fetch. I’ve been editing videos since I was fifteen, but it’d been a while since I cracked open Premiere. I was floored. It’s like I walked away from editing for a few years, came back, and suddenly the robots are generating near-perfect captions for free. Free! The future is here.

>> Everyone should publish their bucket list. Since posting mine, I’ve had two people reach out saying they can help with a few of the items. Do it! The world gets out of your way or helps make things happen.

>> Cash wins at half-time but passion wins the game. I thought I’d be too busy trying to figure out how to make money this quarter that I didn’t expect to do any writing, but I couldn’t help myself. My brain kept wandering back to a project I’ve been wanting to tackle for years, and before I knew it, I was 10,000 words into a new book. Rather than grind out more consulting work, it was easier (and more rewarding) to do what I love. In my bones, I know it will pay off down the road.

Lastly, most importantly, I learned how much I value balance.

I could easily be earning 2-3x more by grinding 2-3x harder, but why?

In three months, I’ve been able to take 3 weeks off to visit friends and family. I’ve unplugged every day at 5pm. I go to coffee shops whenever I want, work from my pool deck, and listen to music nonstop.

It’s pretty great. My stress level is 0 and I am *noticeably* happier.

Am I making millions? No, but I’m more than well off and I trust the process. If I keep inching toward my long-term goals, I have enough chutzpah to believe there are more lucrative paydays ahead. Even if there aren’t, I already wake up every day feeling like I’ve won. Can’t beat that.

What are the downsides so far?

Entrepreneurship is not all sunshine and caramel macchiatos. Here are some of the downsides.

>> Bookkeeping is a bitch. Remitting HST and taxes, paying your own CPP, and tracking invoices and expenses takes getting used to, and I’m too cheap to outsource it (for now). Bless whoever does this for a living.

>> I miss work trips. As an executive, it was fun visiting new places, expensing good food, and meeting interesting people. One time, I remember traveling to Boston, Ottawa, New York, Las Vegas, and Trinidad all in one month. What a laugh. Now, there’s no excuse I can make to travel, and even if there was, I probably wouldn’t because *cue next bullet point*…

>> I’ve become way more frugal. When every dollar you make comes from your own business, you guard your bank account like Smaug. I wish I could relax like I used to — especially since I’m making more than I was as an exec — but there’s always a little voice saying it could vanish tomorrow.

>> No one cares about your work as much as you, and that’s ok because they don’t have skin in the game — just don’t expect extra hustle. I’m always the one who has to push for more aggressive deadlines, check-in on progress, and ping people multiple times.

>> Everything is unpredictable in year one. Example: seasonality. I had no idea that most consulting jobs would dry up in August. Who knows what else awaits in the months and economic environment ahead?

Dios mío, I didn’t forsee consulting drying up in Aug. Happy that September is back on track.

What's next?

Being a dad and figuring out how to parent two Tasmanian devils is my #1 priority for as far as the eye can see. If all I accomplish is that the kids don’t burn down the house next quarter, we’ll call it a win.

Professionally, I’d be lying if I said I haven’t been thinking about how to achieve my long-term goal of becoming a full-time writer / creator faster.

As Peter Thiel says, figure out how to achieve your goals in 6 months.

Six months might be pushing it, but I like the sentiment.

I’ll continue consulting to pay the bills, but, beyond family time, I’m going to focus more on content and creator work next quarter — specifically, scaling analyst projects and finishing my next fiction novel.


1. Be a damn good dad. KPI: Take 2 weeks off for newborn and cut back on work 20% over the next three months.
2. Finish first draft of new novel. KPI: Write 90,000 words.
3. Maintain consulting income. KPI: Do 2 consulting calls per wk.
4. Scale analyst rev. KPI: Complete 1 analyst series per mo.

If I can do those 4 things, I’ll be happier than a mosquito on a nude beach.

Till next time!

Wait, what about the kidney stones?

Shit. Why’d you remind me? I’m trying to forget about that.

So here’s the deal. I woke up a few weeks ago like I’d been shot in the back. My first thought was appendicitis because my brother’s had it before.

Cut to the hospital and a doctor saying I have a 4mm stone that can’t wait to meet me. Given its size, there was a greater chance of passing it than not, so he slapped some my morphine in my hands and sent me home.

Fun fact about kidney stones: the most painful part is not actually passing one, but the trip it takes from your kidney to your bladder. The tube (ureter) it travels through is small and not meant for solids. Picture trying to shove a grapefruit through a toilet roll.

Once I was home from the hospital, things were fairly easy. Other than the pain, the worst part was not being able to complain about it to my pregnant wife for obvious reasons.

With that behind me, the rest of the year should be a breeze. Consulting? Pff, easy. Writing books? Puh-lease. If I can piss rocks, I can do anything.

Pictures from the field this quarter

Things I was obsessed with this quarter

>> Old Stephen King interviews. Examples: this one, this one, and this one. I’ll put them on like podcasts when doing dishes or errands.

>> Pool care. After hosting a couple pool parties, our water was permanently teal no matter how balanced we got the chemicals. The solution after much testing? C-pool. I now know more about pools than I ever cared to know.

>> Sequels. H’oooh boy. With Return to Monkey Island, Hocus Pocus 2, House of the Dragon, and Rings of Power all coming out in Aug / Sep, it’s an understatement to say I’ve spent a lot of time watching trailers, interviews, first episodes, and online theories.

>> Game Changer. I recently found out one of my favorite comedians, Josh Ruben, starred in a show for College Humor called Game Changer. It’s the funniest shit ever. Watch an episode here. (Fun fact: I once hired Josh to promote one of my books. Mr. Gerbins killed it.)

>> Chess hustler videos. Every few years I go down a rabbit hole watching chess hustlers on YouTube. Some faves here and here.

>> Scrivener. Scrivener is a writer’s dream. I’ve always written books in MS Word, but Scrivener is my new favorite tool, especially for novels. It’s a way better way to organize chapters, characters, scenes, research, etc.

>> Hadestown. The soundtrack from Hadestown is incredible. I think I’ve listened to this particular song 11,000 times in the last three months.

>> Storyworth. Best product of the year (decade?) goes to Storyworth. It’s a service that emails your loved ones questions once a week and turns them into a book at the end of the year. My mom just finished her book and it’s the best keepsake ever. Everyone should do it.

>> 2012 Cabernet Franc from Redstone. New favorite wine in Niagara, easy. Nicole took me out on a date night and they had half-off domestics, so I got a $100 bottle for $50. Steal! If you’re in Beamsville, hit them up.

>> The ticking in our basement. Ugh. For months now, there’s been a ticking sound in our basement that no one can figure out. We’ve had HVAC techs, plumbers, and trades friends investigate and no dice. Next call is Ghost Busters before I start knocking down walls myself.

That’s it, that’s all. Catch you in another three months!


Devon Hennig

Devon Hennig is a writer, marketer, and ex-game-show host. He quit his job as a software executive to make a go of it on his own. Follow along as he tries not to go broke.

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