Rox’s Picks 37

Hi friend,

Huge, huge, huge news in today’s newsletter. But first…

I’ve added an extra segment of the newsletter. Courtesy of my amateur photographer-sister Rianne, every edition of my newsletter now gets a custom header image. 🤩

Give her a follow on Instagram @viewfrommyinstax.

OK, on to the news.

After a couple rapid rounds of interviews, I said yes to my dream job this weekend. In September, I'll officially be starting my role as Convictional’s first growth engineer/marketer.

For the next 4 weeks, I’ll be winding down my business and my part-time job. Then I’ll take the rest of the summer off to rest and prepare for this new chapter in my life. In this newsletter, instead of my usual links, I go into detail on my decision-making process for the job.

A major shout-out to Ryan for the initial hook-up with the job description. KBBQ’s on me, dude.

Last week’s newsletter had a 53% open rate. The top links you clicked were this Notion database of life-changing essays and Julian Shapiro’s Writing Handbook.

Here’s what I worked on this week:

[New Article] Why Asians Aren’t Drowning in Debt (But North Americans Are)

The essay is about why I happily clean my own toilets in Canada, versus having maids do it for me in the Philippines… And how I am totally OK with that.

As I mentioned in this tweet …

… This article is one of the absolute best pieces of writing I’ve ever published online.

The essay is full of stories, lessons, and ideas on wealth that, if you grew up in the West, you probably had never thought about. Like my True Wealth Pyramid:

Anyways, if you don’t read anything else in this newsletter, please read the essay.

If someone forwarded you this email, you can subscribe below and get this every week.

Here’s what I learned, shared, and paid attention to this week:

Usually I share my favourite links… But this week, I’m sharing my decision-making process on what made me give up the freedom of my own business to go back and work for someone else.

After I walked out of the Shoelace offices in 2018, I swore that that would be the first and last full-time job I’d ever take. But then last Sunday almost exactly 2 years later, I signed on to start full-time at Convictional, another tech startup.

What changed? Well for one, I’m older and wiser. I signed the dotted line only after the company and the role fit my checklist perfectly.

Like I told the Convictional team, the only thing that would get me to drop my business would be the opportunity to become the Andrew Chen or Brian Balfour at an up-and-coming tech startup, preferably in ecommerce or direct-to-consumer (DTC).

And I didn’t want to work for another SaaS startup, either.

I wanted to start, build, and scale a marketing team at the platform or aggregator level (think, Shopify and Amazon).

The fact that Convictional is a business-to-business (B2B) company just sweetens the deal for me.

In this email/essay, I’ll go deep into the 3 main reasons that persuaded me to go back to work for someone else:

1. Mastering marketing

2. Working in B2B

3. Building marketplaces, platforms & aggregators

Mastering Marketing: Breaking New Ground

There are two things I can’t do with my own business at the moment:

1. Solve the biggest marketing problems in the world

2. Build a world-class team

As a consultant, I work with clients whose problems I already have the answers to. No sense taking risks if my retainer and my rep are on the line!

As a solo business owner, I keep my payroll lean with freelancers — people who can do the job well enough, but not great.

In contrast, becoming a successful growth marketer is less about doing what already works, and more about pushing the technological limits on what could possibly work.

At Convictional, I’ll break new ground, looking for opportunistic channels that have short-term gains and long-term promise. My main mission is to quickly test paid, earned, and owned marketing channels for the company. Long term, I need to build a marketing flywheel that will compound those wins over time.

As Brian Balfour says in his article “7 Principles to Mastering Growth,”

As the first marketing hire in a company of 10, I have to do everything myself. But being the first marketing hire gives me another special privilege: I get to build a world-class marketing team.

Hiring people and building a team taps into a secret superpower that none of my previous employers or clients have used. I can read 80% of the people I meet like a fiction book, instantly and accurately. I just know people. In fact, I’ve been accused of being a mind-reader like Donna in Suits.

In my opinion, cracking marketing and scaling a team at a YC-backed tech startup that’s carving out a new road in a well-trodden path like B2B, is one of the most difficult, prestigious, and rewarding challenges a young marketer can face.

And this excites the hell out of me.

Working in B2B: Taking Advantage of What I Know

Entrepreneurship is about developing valuable ideas around knowledge that other people don’t have. It’s about executing against secret information and a different set of knowledge corridors than other people.

I’ll let you in on a secret most people don’t know: 

It’s this insider’s knowledge of the untapped frontier of B2B ecommerce that serves as Convictional’s unique selling point.

Let me explain.

B2C companies like Apple, Facebook, and Muji hold all the sex appeal. They have to appeal to the masses with attractive branding. Otherwise, they don’t grab attention. They can’t compete. They don’t sell.

But it’s in the B2B world where the most lucrative deals hide. Sure, deals take more time because B2B is notoriously bureaucratic and can be frustratingly nepotic. But once you’ve built that relationship and struck that deal, particularly if the deal’s wholesale (possible recurring revenue without extra selling) or software (build once, sell in perpetuity), you have it made.

You get volume purchase orders.

You negotiate manufacturing terms with economies of scale.

You have financial runway.

Convictional aims to help speed up that process of B2B relationship-building and deal-making. And thanks to my upbringing in the family business, I know enough to jump on a good deal when I see one.

Building Marketplaces, Platforms & Aggregators: Raising the Ceiling

If my highest ambition was to be a lifestyle entrepreneur or a digital nomad, then I was well on my way to achieving that with my business. In fact, I was planning on travelling more and trying out the remote life in 2021 (this was before COVID hit).

But like Harvey Specter, I say, “Life is this… I like this.”

And so, courtesy of Nathan Barry’s wealth ladders illustration, I’m taking a job that lets me go from this:

To this:

As you can see from the illustration, skills- and compensation-wise, there’s no higher place for a business to go than at the marketplace level or, as Ben Thompson calls it, the aggregator/platform level.

To relate this idea to my first and second points, doing marketing for an aggregator or a platform means I’m working on the toughest and most financially lucrative problems in the world.

No cap.

Why I’m OK Giving Up My Freedom to Work at a Job

I wasn’t optimizing for wealth or freedom when I signed the contract.

My only financial requirement was that the job pay me enough to get my own place in Toronto. Once that was settled and I was convinced that this was the chance to solve the biggest marketing problems in the world, I was more than willing to concede my freedom as a solo business owner.

Honestly, though? I don’t feel like I’m giving anything up at all. 

Working at Convictional removes the impact, reward, and difficulty ceilings for my career. Working at a company frees me from distractions like cashflow, bookkeeping, and client pipelines that take my attention away from a singular goal — marketing an IPO-worthy idea. The company is also (thankfully) 100% remote so I’m still in charge of my own schedule. I’m pumped to be free to pursue the most challenging marketing problems in the world… Problems that also hold personal significance for me and my family.

Taking this job at Convictional is my dream job, not because I’ll "never work a day in [my] life." I didn’t say yes because I don’t foresee problems. In fact, this job terrifies me because it’s going to be a lot of work, a lot of failure, and a lot of headache.

But it’s perfect for me because it lets me obsess over problems I want to deal with, while eliminating ones that I don’t.

That's it for this week!

Stay strong, stay kind, stay human.

Till next week,

Roxine

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