The Startup
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The Startup

20 Lessons From Building & Selling My Side-Hustle

Four years ago I pulled the trigger: I founded a startup, supplementing full-time employment. Solo and bootstrapped, it truly was a hustle — countless long nights and working weekend only intensified existing work.

After servicing clients from around the world, appearing in international press, and kindling strategic partnerships, my side-hustle, now poised as a full-time business, has been acquired.

My baby was PRSNL Branding, an education platform and consulting studio, enhancing professionals’ online presence to advance their careers. After all, how you appear online dictates job prospects. Delivering everything from résumés and LinkedIn’s, to personal sites and online privacy guidance, PRSNL helps people stand out creatively, strategically and professionally.

Over the years, I picked up invaluable business lessons that I otherwise would not have gleaned from on the job, amongst a class, or within a book. Below are my learnings and observations that I see as invaluable for anyone thinking about, or actively pursuing a side-business. Godspeed.

01. Own Pride

There is truly nothing more rewarding than callousing your hands on something that you get to call your own… and then reaping the upside. Calling your own shots without hierarchy or politics is what drove me to start something outside of my 9–5. That desert-like sandbox comes with incomparable pride when your name is on the letterhead. If you’re looking for “safe freedom,” start. Now.

02. Bridge Knowledge Gaps

Lean into your weaknesses. One of the most fulfilling parts of growing a side-hustle was exposing myself to my blind-spots. The only thing more valuable than supplemental income is supplemental experience. Challenge yourself and cover your bases around what you don’t know or what you’re not good at. Whenever the side-hustle fades, you’ll have more than money.

03. Re-Define the Metrics

According to mathematician Richard Tapia, “We don’t know how to measure what we care about so we care about what we measure.” There’s a preoccupation with contrived metrics like company valuations and app downloads. Helpful numbers, but hot take: business success could and maybe should be measured by the positive impact you’ve had in the lives of your customers. Chase those “metrics” and the money will likely follow.

04. Remain Lean

Somewhere, somehow entrepreneurs became obsessed with investments and showy financials. Raising money isn’t an end-goal, it’s a loss of equity and control. Bootstrapping is hard, but the snowball has to start rolling from somewhere: early revenue. Spend what you earn. Profits with minor expenses are underrated and much sexier than big revenue and bigger expenses.

05. Make Quality #1

Superior quality of your product or service should be a baseline point of differentiation. Difference in price-point is not a fun game. Generally, going cheaper is a cheap move. Aim for “better” first. Research and audit your competition. Strive to beat them at excellence. Focusing on superiority of output is a lot more rewarding when your name is tied to your work.

06. Over-Service

Customer service is priority number one. Don’t screw it up. Perfect it. When starting something from nothing, reputation and word-of-mouth are the cheapest paths to growth. Bad customer experience eclipses everything you work on. People like nice people. Be nice. Killing customers with kindness is an effective long-term strategy. Reputation is always-on sales.

07. Avoid the 24/7

However, service-based businesses are an ugly beast if you’re the one on-call servicing. Dropping an existing task when you’re managing a full-time gig is a lot. Forced smiles and gritting teeth takes a toll, especially when you know you don’t have to be doing this. Customer experience is key, but don’t let it consume you. I was mindful to strike this balance and still lost.

08. Solve for Variables

Further, customers could be your business’ most important variable — one that’s absolutely unpredictable. Solve for the unknown with standardization, consistency and productization. Listen to what they want and grasp why. Customers are irrational, annoying and cheap. Find ways to protect yourself from their chaos. Understand them and hedge against it.

09. Think Higher

Whatever you’re making and selling, it likely serves a higher purpose. Tool makers don’t sell drills, they sell holes for shelves and clean homes. People don’t want what you make, they want what it will ultimately do for them. Your service provides an even higher service. Consumers are buying better versions of their current lives. Remember that when making and selling.

10. Consider Saturation

You’re going to have more competitors than you initially realize. What makes you remarkable? How commodified is your product or service? I stumbled into an incredibly crowded and sleazy space, which I don’t regret, but was unprepared for. I was alongside tons people fighting for attention. Position yourself or go somewhere where you’re alone. There, work will come to you.

11. Be Niche-r

The long tail is where it’s at. Being #1 for a fraction of the world is more rewarding than being #100 for every- or anyone. Go deep. Specialize. I tried to service everyone at first, and never prioritized who I was for. Force yourself to explore and prioritize. Start with one thing and perfect it first. Niche is nice. With that, create a brand that can grow with you.

12. Become Symbiotic

Symbiosis is a mutually beneficial relationship. Create lots of them. When small, partnerships are invaluable as money and momentum isn’t on your side. Identify opportunities to help others while helping yourself via collaborations, residencies, or white-labels. Search for and exploit win-win opportunities. Create external teams that end up just working for you.

13. Hide & Seek

As a brand-guy, when beginning, I was stoked to have my own company image. I spent a lot of time chasing PR opportunities, establishing aesthetics and crafting tone of voice. I will never dismiss the importance of brand, but it’s not everything. Recognize when to keep your cards to yourself and work silently, and when to drum up attention. Work smart, not hard.

14. Thrive as Obvious

Focus on a sector, product or service that doesn’t require education. With an emergent, complex service, I was simultaneously educating while selling. It sucked. If you need to explain why people need you, they’re not for you. There’s a steep hill in justifying your business. Go to spaces where people are already searching for you, but nothing exists. Let your business sell itself.

15. Inhabit the ‘In-Between’

A lot of successful ventures are waiting to be created “in the in-between.” In other words, businesses that address behaviors which already exist, but no entity is capitalizing on. What are universal acts, habits or home-made solves that no one is capitalizing on? Many focus on predicting or creating new problems. That’s hard. Easier, what current white-spaces can be filled up?

16. Do Good

If you’re creating something from scratch, do more than make money: better people, culture or the world. Business and social good can be non-mutually exclusive. In fact at this point, they should be. New ventures don’t have to be a B-Corp or non-profit, but there should be meaning beyond profits — whether you’re tackling mental health, sustainability, education, joy, etc.

17. Focus Sharper

Do. Not. Get. Distracted. Beginning, I was giddy and overwhelmed with ideas and pursuits. After all, I was alone and finally free. This resulted in social media strategies, partnership creations, brand books, college ambassador programs, you name it. There was no compass or prioritization of efforts. It took a year and change to finally focus. Small bites. One thing at a time.

18. Compound Successes

Build a positive-sum business. Each interaction should help the next interaction. Each of my transactions existed in a vacuum. Each new client was a restart. Nothing built upon itself. It was single-dimensional. There was no network effect or accumulated knowledge that serviced others. It was Sisyphean. Let your work and growth compound itself, working for you.

19. Don’t Go Solo

I did and deeply regret it. It’s a lonely journey. Sure more upside, but not as gratifying. Two brains are better than one, and four hands better than two. If you’re alone and you stop peddling to focus on your day-job, the machine screeches to a halt. There’s an incredible peace of mind when someone is working when you’re not. It’s more than business and you should…

20. Have Fun

It’s painfully cliché. But if this is not enjoyable, why are we doing it? If you’re fortunate enough to manage a side-hustle, catch yourself before you let it become a burden. That’s not to say it can’t be challenging, demanding or even stressful, but when resentment and boredom eclipses stimulation and your well-being, consider moving on. Don’t punish yourself. We’ve got limited time here, let’s make the best of it.

And with that, enjoy. Onto the next one…



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Matt Klein

Matt Klein

Cultural Theorist + CyberPsychologist + Strategist. Trends Lead at Reddit. Newsletter analyzing the overlooked: