6 Lessons for Entrepreneurs (That I learned in 6 years of running Propr)

6 Lessons for Entrepreneurs (That I learned in 6 years of running Propr)

November 17th is Propr’s birthday, and this insane year of 2020 marks six years of helping develop and differentiate brands through our integrated approach to holistic brand strategy, design, and marketing. I’ve also learned a lot of things. I hope sharing them will make your transition to a brave entrepreneur easier and more efficient.

After 21 years in the industry, I find myself, in the wake of an election and the massive shadow of an ongoing pandemic, reflecting on six exciting (never boring) and successful years of owning a company and being an entrepreneur.

To be an entrepreneur is to be an optimist. We believe the future can be better, and we shoulder the responsibility to make it happen.

1. Nobody knows what they are doing

Yep, believe it. It’s real, and don’t let people front or act like it’s anything different. If they do, you know they are full of shit. The only difference between a new entrepreneur and a vet is the amount of time you’ve been at it. You’ll get there soon. Please don’t feel intimidated or compare yourself to other business folks because it’s usually always a false equivalency. Rarely are entrepreneurs trained, coached, and groomed for their big jump. Don’t sweat it, be yourself, do your due diligence, follow your vision, and build confidence through your experiences and learning. 

2. Overnight success is bullshit

Ignore these clickbait stories that show up frequently. While it makes a great and very dramatic story, it’s always a myth. “Overnight” typically means a decade in business and a few million in investor money. The perception of overnight success hinges on entrepreneurs seizing on a shift in the market, nailing a new opportunity, or their years of hard work and product/service value are finally recognized by the market, launching them into a very successful situation. 

Forbes on The Overnight Success Myth

3. Always keep it in beta

Set it and forget it? Fuggedaboutit. You’ll be well served to remain curious and look for ways to continually improve yourself, your brand, your team, your products and services, and all aspects of your venture. It’s pretty simple, show up, and take the time to learn and grow. Don’t fall into dangerous mindsets like: “this is the way we’ve always done it” or not focusing on the future because you’ll fail if you do. Definitely seek out wise mentors, positive colleagues and influences, helpful books and blogs, quality coaches, and informed advisors to maintain your edge and continue to be a competitive and likable brand. However, sometimes good enough is good enough, but recognize the signs when good enough is holding you back and be prepared to invest in improvements to take you to the next level. 

Check out Bobby’s COVID reading list for entrepreneurs


Are you looking to grow your business with a stronger brand?

4. Don’t stop marketing!

No matter what, invest in strategic marketing for your brand to remain top of mind, beat back the competition, and maximize opportunities when the competition foolishly cuts its marketing back. Staying top of mind with your audiences doesn’t have to cost money or be massive campaigns. Just make sure, especially in these crazy times of constant disruption, to let your customers and audiences know you’re still out there, doing OK, and happy to serve them. If you don’t your competition will. And if your competition is lunching, seize that opportunity and win. 

Read more on how to market like you give a shit

5. Just say no

I get it, during the first few years of Propr I took on some freelance work, contractor work, and put myself out there as a hired gun, and more.  Hell, I needed income, and who doesn’t? I was very self-aware and knew this was always a temporary situation since my focus was on achieving my vision to grow an agency. But I wish I said no to that work earlier. There are still things that come up that I say yes to and later regret. Here’s the lesson, knowing the difference betwixt good money, and bad money is critically important. Keep learning, evaluate during and post-project, and strive to be wise and savvy, and never say yes to the wrong fit. Obviously, this is easier said than done, but the wrong work will only distract you from your vision and goals and make them increasingly harder to achieve. Say no early and often.

6. Brand = reputation

It’s not what you say about yourself and your brand that matters; it’s what others say and think about you. Thinking of your brand as your reputation puts it in relatable terms since it’s all aspirational, and one wrong move can ruin it. Remember, people don’t always remember the last interaction with your brand, but they remember how it made them feel. Don’t screw it up.

Read more about why your brand matters more than ever

Bonus Tip

You don’t have to put your time in all over again. Taking the plunge as an entrepreneur doesn’t mean you’re starting over and have to build up your street cred all over again. That’s wrong; you take your experience, instincts, expertise, and ideas with you. So don’t do things like charge too little or be timid in negotiations. Be proud and confident. And if you need help composing your story, building your brand, and confidently kicking in doors and disrupting the game, Propr can help. 

Need help building your brand? We got a killer Workshop for that


Bobby Gillespie


With 24 years of creative experience in leadership, planning, and executing performance-based branding and web design strategies, Propr and I help small and medium-sized companies and organizations grow revenue, attract new customers, manage and scale their brands, and improve marketing performance.

I’m also the author of Build Your Brand Like You Give a Shit.
Connect and follow me on LinkedIn.

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About Propr

Propr Branding and Web Design Best of Maryland Awards

Propr is a boutique brand strategy and creative agency. We help companies and organizations grow through high-performing brand strategy, graphic & identity design, messaging & custom WordPress website design & development. Performance and results drive our passion for service. Let’s do great things for your brand together.

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