Momentum Matters: 5 Lessons I’ve Learned in 5 Years

LinkedIn Newsletter

I started a newsletter last week using beehiiv ! I've been mulling over cross posting it on LinkedIn as well, but had a hard time deciding. I prefer the intimacy of a 1 to 1 channel like email much more than posting on LinkedIn. However, I realized I have thousands of LinkedIn connections compared to the ~700 people in our CRM.

Ultimately, I decided it makes sense to post an edited version of this newsletter for wider reach.

If you'd like to sign up for the actual email newsletter, you can sign up here .

Why Am I Starting a Newsletter?

The honest answer is that I think it’s more and more difficult to stand out in the affiliate space. The space is crowded. Two years ago, I made a goal to actively post on LinkedIn. As we’re more established and have a number of highly reputable brands under our umbrella, posting on LinkedIn feels inauthentic and congratulatory. So, I’m toying with a new format. I also love talking to clients and learning about their businesses. I’m excited about the conversations that will follow, so please reply to me with your thoughts.??

Separately, writing a newsletter is an exercise in self-reflection, so it’s a good opportunity to reflect on our journey and how our industry is evolving.?

Why “Momentum Matters”??

Every entrepreneur brings a flavor of themselves to their business. I’ve always been someone who tries to anticipate where the puck is going and stay ahead of the game. In terms of executing, though, I’m a huge believer in momentum. Momentum compounds. You just have to start, not unlike this newsletter. Half the journey is starting and the other half is staying alive.?

5 Things I’ve Learned in 5 Years?

As we near the 5th anniversary of starting Hamster Garage, I wanted to reflect on 5 things I’ve learned building Hamster Garage.?

#1: You Chip Away at Fragility Year by Year??

In 2019, I left to start Hamster Garage with Airbnb as our first client. Less than a year later, the world went into lockdown. Airbnb shut down all host marketing. My former colleagues at Airbnb all lost their jobs and we lost our flagship client. By chance, we had been in talks with a then little-known, unicorn startup called Canva, which decided to take a chance on us over bigger, more established players because of our more strategic approach.?

Over the next few years, as Canva’s valuation ballooned from $3B to $40B, we had the best client + agency relationship an agency could dream of. Talk about luck. We could have gone out of business that first year, and maybe if I knew better, I might have closed shop and sought higher grounds.?

Over the next few years, Hamster Garage has had a testing, all-in moment once a year. But each year, it was a bit easier. We won more clients. Our team grew. We further refined and documented our processes.

The lesson: Most businesses are very fragile early on. You chip away at the fragility each year. Hopefully, half a decade in, you’re a more resilient organization.?

#2: Selling is the Worst Way to Sell?

I’ve been “CEO” for 5 years now, but what does it mean to be a CEO of a 3 person team? I only really started feeling like a CEO in the last 9 months as I spent more of my mental energy thinking about budgeting, forecasting, growth, etc.?

For the first 4 years, 80% of my energy was focused on sales. Thankfully, I love talking to potential clients, so this worked for me.?

Am I a ‘sales’ guy? I’m not sure. I’ve never done sales inside a mature organization. Everything I’ve learned I’ve picked up from reading, conversations and lots of trial and error.?

When I think back to why we were able to win Canva’s business 4 years ago as a >5 person organization, the answer is obvious. I spent 8 months going back and forth sharing insights and talking about how I would approach things. I don’t even remember if we ever had a formal pitch as much as a long email thread that ended with “Let’s figure out a pilot for us to work together. Send a statement of work.”?

This quarter, we revamped our sales process after I realized why Canva picked us: they got to experience who we were before they even signed us.?

For those 8 months, I was hardly ‘selling’ – it helped that our stakeholder at Canva and I both had a ‘move fast and try things’-personality.? If you have to work hard to sell a client to want to work with you – different from a client wanting to work with you but negotiating on the specifics – you’ve already lost.?

The lesson: Don’t sell. Educate, debate and discuss.? Let the sale happen by itself.?

#3: Operate like a Sports Team

A corollary of being future-minded is that I’m an optimistic person. I love imagining where the future is headed. If I focus on Blue Oceans instead of Red Oceans, I can win without getting lost in margins and granular optimizations. This has contributed to Hamster Garage being an upbeat, exciting place to work: we’re always looking ahead.?

This uplifting vibe can make it feel like we’re a big family. However, I think this perspective is mistaken.?

Reed Hastings, the founder and co-CEO of Netflix, recently spoke at Stanford GSB and described working at Netflix as akin to being on a sports team. You’re drafted into a team and expected to perform at the caliber of your teammates and to make the franchise successful.?Something clicked for me hearing this: I think it’s the right analogy for running a high-performing company or really any team.?

Our clients come to us because we’re a team that is strategically-minded and tries to maintain a high bar for execution. If we hire someone who is unable to meet that bar, it’s unfair to let that person remain on the team at the cost of everyone else and our clients. A-players leave when others aren’t pulling their weight.?

We have a young team that we hire from top universities, so our equation is more complicated since we have a responsibility to train and build our talent too. However, there’s a clear line between growing someone who’s ambitious, hard-working and talented and someone who has become complacent.?

The Lesson: Operate like a sports team. Make tough choices, but don’t lower your bar.?

#4: 0 to 1, 1 to 100?

I’m a 0 to 1 person. I love thinking of an idea and making it come to life. As an entrepreneur, this is an essential skill. Being able to build despite limited resources is the essence of being a founder.??

However, as you scale, it’s important to consider if the 0 to 1 approach is benefiting you or harming you.

I built our first ever site on Webflow. Getting a designer abroad to build a simple site for you can run about $3K to $5K. Stumbling your way around Webflow by watching tutorial videos, leveraging a $39 template and spending a weekend or two is scrappy. Five years in, we’ve redone our site a few times. The last time around, I still built it myself. Moving forward, however, if we were to do it again, I’d hire someone instead.?

At this point, it makes more sense for me to use my time to go after the thousands of underserved large brands on Commission Junction and Rakuten than to learn more advanced Webflow to build a spiffy site. It’s not easy because I actually love learning new tools and playing around with design, but I’d be doing a disservice to Hamster Garage. My time is better used elsewhere.?

The Lesson: Know where you can provide the most value, and know that it’ll change over time.?

#5: Enjoy the Journey?

Many of the lessons I’m sharing are part of the natural curve of building a company. You can’t rush the journey. In these 5 years, I’ve closed enterprise clients that a 24-year-old me would have never imagined, I’ve bought a YC-startup, I’ve had to fire people, I’ve dealt with lawsuits, and I’ve spent more time evaluating payroll providers than makes sense. It’s been quite a ride and it’s far from over.?

Each of these instances happened when the company evolved to a point where it required me to dive in and figure out how to do it. There were certain insights that clicked at different points that didn’t click at earlier points, and that’s to be expected. Over the years, insights from other entrepreneurs further in their journey clicked as I’ve experienced similar situations myself.

Said another way, it’s important to appreciate exactly where you are at. We live in a time and society where work is a huge part of our lives. We all work a lot. It’s imperative that we celebrate the milestones and be patient with our own growth.?

Celebrate the client win. Celebrate the new office. Host the retreat. Host that end-of-year holiday party. Take the week off.?

The lesson: If you’re not enjoying the journey, you’re probably on the wrong ride.?

That’s it – that's the first edition.?

I haven’t figured out the frequency yet, but once or twice a quarter feels about right. This issue focused on my learnings, but moving forward, I’d love to share information and insights about the affiliate space and technology in general.??

I genuinely value your engagement and perspectives. If any part of this newsletter resonated with you, sparked an idea, or if you have insights of your own to share, I'd be thrilled to hear from you. Your thoughts and feedback will help shape the content of future issues!?