I Built, Scaled, and Sold a Side-Project-Turned-Business. Here Are The Most Valuable Lessons I Learned Along The Way.

In the beginning of 2020 I attended a wedding with a good friend from business school. We had started to follow the news of the emerging Covid outbreak and discussed how the world might be altered as a result.

Of course we had no idea that the world would change so profoundly.

But we had an intuition that we should collaborate, assemble a team (by adding a childhood friend to the core operation), and build something that could help people if work or commuting habits changed.

As lockdowns arose, first in other countries and then the US, we knew that some people would transition increasingly to remote work.

This insight was reinforced when our own offices were shut down.

Our North Star was simple: build a set of products to help workers switching from corporate to home offices.

We felt well positioned to add value in this market segment since we were spending so much time thinking about our own home offices, remote careers, and the struggles our friends and colleagues were experiencing on a daily basis.

After brainstorming different approaches, we settled on a name (WFH Adviser) and defined goals and milestones. We didn’t spend too much time on balanced scorecards, the four Ps, GTM planning, or the Five Forces.

We started building and got to work.

Fast forward 2.5 years: the site we devised morphed into a business that generated predictable, protectable, free-cash flows.

We helped serve over 250,000 customers.

And in Q3 of 2022, the business was acquired.

Events close at hand are hard to judge without the proportion that time lends.

Yet with the acquisition recently completed I wanted to reflect and write-down my most salient learnings in order to:

1. Help other builders. Hopefully the insights that follow can help you — a founder, product builder, entrepreneur — more readily find product market fit or identify ways to monetize or scale your technology.
2. Capture the lessons we learned along the way so that we are better suited to remember what worked (and what didn’t) so that we can do a better job of building our next side project, Ring Advisers. As Harry Truman noted: “There is nothing new in the world except the history you do not know…”

From conceptualizing an idea to bootstrapping a business to an acquisition, here are the key takeaways that we found to be true.

Lesson 1: Obsess over the satisfaction of customers and their happiness with your product.

It took roughly 48 hours from the start of our site to the time we made our first sale. This early feedback indicated to us that we were on the right path. We could have taken our foot off the gas, but we did not.

We spent a huge amount of time —on our nights and weekends — talking to users, figuring out what they cared about, and understanding how we could best serve and help them.

No detail was below us: customers could email, DM, or contact us directly.

Many did.

By listening to what people actually wanted help with we were able to best build and craft our product roadmap.

This led to better features and content, which led to more delighted users. The flywheel started to spin, and, as a result, sales accelerated.

“We see our customers as invited guests to a party, and we are the hosts. It’s our job every day to make every important aspect of the customer experience a little bit better.” Jeff Bezos, Founder of Amazon.com.

Lesson 2: Own it (the business, the work, the inputs & the outputs).

When you start a side project, you have to own all aspects of it. You can’t delegate or neglect work: progress won’t be made!

Everything becomes your job: product design, user testing, fixing bugs, setting up bookkeeping, filing taxes, acquiring users, and so on.

Being an owner is hard, but ultimately worthwhile if you can take a longer-term perspective.

“Only buy something that you’d be perfectly happy to hold if the market shut down for 10 years.” Warren Buffett, CEO of Berkshire Hathaway.

Lesson 3: Never stop learning, never stop asking questions. Always remain curious.

Builders (owners, product designers, etc) are never done learning.

We always found new ways to learn and grow. Some days it was about the current product, other days it was about the future.

We never stopped speaking to customers, industry friends, and partners.

Would you use product feature X? Do you like product feature Y? What do you enjoy most about the user experience? These questions all elicit feedback.

However, these questions are broad. If you want more specific feedback that you can transform into changes to your product (and actionable insights), you will want to ask questions that elicit more details.

By asking the right questions, at the right time and in the right way, value can be unlocked.

“We keep moving forward, opening new doors, and trying new things, because we are curious and curiosity keeps leading us down new paths.” — Walt Disney, filmmaker and co-founder of the entertainment empire bearing his name.

Lesson 4: Go Big in the right domains (and avoid competition!)

When you’re building a product, there are different frameworks you can deploy to think critically about what to build and why.

These frameworks apply to business as well.

When designing a product — or launching a startup — you should answer a few fundamental questions:

Should I enter the market or not?

Who else exists in this market and what are these firms doing or building? What are the costs of entering this market?

Are these costs fixed or variable in nature?

If I decide to exit the market — or stop building or maintaining my services or software — what are the costs?

Who will use my product or services and what do they value or need?

Am I uniquely equipped to help these people or constituents?

What started as a fun project morphed into a business almost by luck. Yes, we thoughtfully evaluated the market first.

But in hindsight we didn’t think or act big enough.

Our thinking led us to generate several million dollars in gross bookings. But we never devised and executed a product road-map to do $50 million or a $100 million in Gross Merchandise Volume. We thought we were thinking really big. But were we? Not really.

A lesson learned for next time.

“Stay far from timid, only make moves when your heart’s in it, and live the phrase ‘sky’s the limit.’” — Biggie Smalls, rapper and songwriter.

Lesson 5: Deliver Results

When we started the WFH business we didn’t take time to reflect on potential exit paths for the site.

There was no need to.

We figured we would build and grow the site slowly over time, collect profits, and pay ownership a dividend.

As sales increased, and traffic expanded, it became clear that our results were becoming more meaningful to industry players. But we never focused on outputs alone. We focused on the inputs that would, over time, drive the metrics that mattered to us as founders.

In the world of SEO, a key funnel metric is impressions. The more impressions a site has, the more clicks it receives.

If each click is monetized it’s not hard to work backwards and figure out the revenue — and profits — of the business. Even when the ball was bouncing our way, we never settled. We focused on the inputs that would lead to the outputs that mattered.

Here are common motives for M&A. If you — as a builder — get the inputs right, the outputs should follow. If enough value is created as an oupt, a buyer might want your asset for the following:

1. Value creation to shareholders,
2. Diversification,
3. Inherent economies of scale,
4. Market share motives,
5. Access to new technology,
6. Vertical/horizontal integration,
7. Cross-selling synergies.

“Surely, in the light of history, it is more intelligent to hope rather than to fear, to try rather than not to try. For one thing we know beyond all doubt: Nothing has ever been achieved by the person who says, ‘It can’t be done.’ — Eleanor Roosevelt, the longest-serving first lady of the United States.

Lesson 6: The need for information is universal.

Our business was predicated on a simple belief: we could gather information from the internet and help people have better experiences working from home.

This insight proved to be right.

Even though we were directionally correct, we had many missteps along the way. Yet the core kernel of truth is that information — rich content, useful insights, helpful guides — is valuable.

People from all walks of life, geographies, professions, and ages needed help during the core part of the pandemic lockdowns to understand WFH jobs, products, and market trends.

“Always work hard on something uncomfortably exciting.” ― Larry Page, Founder of Google.

Summary

Building a side-project-turned-business, and experiencing the acquisition of that business, was educational, enjoyable, and ultimately worthwhile. We experienced beneficial tail-winds:

1. Our technology costs scaled at a rate one order of magnitude lower than revenue. We could not have built our company without cloud technologies.
2. The content we produced was helpful to users, and thus rewarded by Search Engines.
3. Our premium quality helped us build a premium and respected brand.