7 Lessons for New Entrepreneurs

Bobby G’s 7 Lessons for New Entrepreneurs

Where has the time gone?

It is surreal to think I have been a business owner longer, by nearly three years, than any job I’ve had in my life. While I’ve done many things over my career, being a business owner at Propr has been the most fulfilling and least boring (it ain’t boring, but it also ain’t easy) adventure of my life. While I have learned many things over the past seven years, here are my top seven lessons for new entrepreneurs I have learned in business so far. 

I rarely talk in absolutes or with total certainty because these are signs of someone not open to new ideas. However, these lessons ring true year after year. I wouldn’t say these are business gospel, but I’m beginning to think there may be something here since the people and brands we have worked with over the years have reinforced these lessons as important to sustainable success.

This article spawned the early outline for Bobby Gillespie’s provocative book, Build Your Brand Like You Give a Shit. Available on Amazon.

After seven years in business, here are my 7 Lessons for New Entrepreneurs for consideration.

1. Chill, nobody else knows what they are doing either.

Many entrepreneurs, the business community, and the media like to project an image of the calculating, brilliant, put-together professional visionary. But the reality is that people are figuring it out as they go, which should comfort you. Sure, we may have a vision and experience, but all the struggles and challenges we face aren’t uniquely yours; we’ve all been through there, are there,  or will eventually be there. So relax, don’t fake it till you make it, keep it real, seek constant improvement, find the helpers, and do what you need to do to build genuine confidence through knowledge and experience. 

2. We can’t predict the future but must commit to thinking about it.

A once-in-a-lifetime pandemic can teach us a lot of things. One common takeaway is that we can never predict the future but must commit to thinking about it. I advise our clients to have a five or 10-year vision for their brand but only plan out 6-months at a time. Anything more than that is a fool’s errand and a wasted opportunity. That’s because so much can and will change, and with developing and marketing your brand, slow down, take imperfect strategic action, and then review, assess, evaluate, and improve your efforts every few months. You’ll see more substantial returns less waste, and an agile, informed strategy will ensure a healthy brand and more sustainable growth. 

3. Always give people the benefit of the doubt.

Shit happens, and when we are frustrated by things like getting stood up for a meeting or not hearing back from someone, we are left to speculate, and when we speculate, we often go down a dark path and think the worst. Avoid these negative thoughts, and give folks the benefit of the doubt. Perhaps something came up or worse. Check in with them, leading with “I hope everything is OK, sorry we didn’t connect,” or something of that ilk. You’ll avoid driving yourself crazy or embarrassing yourself by sending an angry message you’ll regret later. If they did blow you off, good, they showed their hand, and you can stop wasting your time and move on. 


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4. Be deliberate about who you let into and keep in your village.

Some lessons I’ve learned the easy way, some the hard way. This one, I’ve learned the hard way. There is no question that some people in this world are takers; some people are givers. I see myself as a giver, and at times, my kindness and generosity leave me vulnerable to people ready to take advantage of that. I’m OK with that. But toxic people are out there, and once they show you where they are, the best thing to do is boot them from your village and move away from them as quickly as possible. On the flip side, some people share your values and principles and genuinely want to see you do well for no other reason than they like you. Seek these people out and keep them close. And strive to be that person, too; kindness is the secret to happiness, despite what we’re told. Keep this in mind for every aspect of life, personal and professional. Who we are at Propr. 

5. Empowerment and trust start at the top.

Trickledown economics is total BS, but trickle-down trust and empowerment are not. Leaders and managers who micromanage or spy on their teams poison the very companies they work for. As leaders, we must weed out these people who allow/enact this type of management because the folks who don’t trust their employees and teams are the ones who aren’t worthy of being trusted themselves. Trust is earned and incredibly fragile, of course, but only trustworthy people can trust others. Yes-men, micromanagers, people always covering their asses, liars, people who never hold themselves accountable, et cetera. are dangerous to your brand and culture; do what’s best for your brand and remove them immediately.

6. Communicate, compete, and connect through your values.

Your core values are a non-negotiable part of your brand. When you use your values to communicate, you’ll lead with authenticity. When you use your values to compete, you won’t have any competition because no one can compete with you on being you. When you use your values to connect with people, you’ll inherently make more meaningful connections because you’ll be more relatable and likable. People who share your values get drawn to you; customers who value the same things as your brand become fans and supporters, and you’ll enjoy engaging with them. People who disagree with or don’t share your values will stay away; it is a win-win situation. Plus, it’s authentic, so there’s no need to push a false narrative or front, which is never a good idea. Need help defining authentic and actionable values, positioning, and messaging for your brand? Check out the Propr Brand Strategy Workshop. It’s exactly what you need. 

7. Relationships > transactions.

The world has become overly transactional, especially the business community. (The agency world is even worse; this is one of the top catalysts for me to start Propr.) For example, when companies put a CFO in the CEO seat, instead of setting the vision for the brand and acknowledging and celebrating the people contributing to its success, they are looking at how to cut costs, like making layoffs to improve line items on spreadsheets. We see short-sighted brand-damaging decisions like commoditizing talent, leading to top performers and contributors getting let go. Or they are reducing product quality to save a buck, cutting back service and support to elevate margins. Transactional focuses like these damage all aspects of service, product development, morale, and your brand’s reputation, limiting your brand’s potential. 

Bonus: Perfection doesn’t exist; don’t chase it.

Stop pursuing perfection. The only predictable outcome from pursuing perfection is paralysis or procrastination. Instead, set your bar for what good enough looks like to your brand, do your due diligence, and take imperfect strategic action. Then, learn from your effort to iterate and improve. 

Propr helps clarify and activate growing brands to scale. Get in touch if you’re ready to be empowered to grow your brand.

Top 5 Brand Books for Entrepreneurs & Business Leaders


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.

Schedule a call to learn how we can help you transform your brand for consistent and better performance.

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.

Ready to transform your brand for consistent and better performance? Contact us today!

By: Bobby G


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12 Success Tips for Aspiring Entrepreneurs

By: Bobby G    05/2020

12 Success Tips for Aspiring Entrepreneurs
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