Bobby G’s 7 Lessons Learned in Business After 7 Years

Bobby G’s 7 Lessons Learned in Business After 7 Years

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 has been the most fulfilling and least boring activity of my life. While I have learned many things over the past seven years, here are my top seven lessons learned in business. 

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 go as far as saying 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.

My top 7 lessons after 7 years in business, for your 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 be comforting to you. Sure, we may have a vision and experience, but all the struggles and challenges you face aren’t uniquely yours; we’ve all been through there, or 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 we 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 we 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, 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 that you’ll later regret. If they did blow you off, good, they showed their hand, and you can stop wasting your time and move on. 

4. Be very 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, who 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 real secret to happiness, despite what we’re told. Keep this in mind for every aspect of life, both personal and professional. 

5. Empowerment and trust start at the top.

Trickledown economics is total BS, but trickle-down trust and empowerment are not. Leaders and managers that 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 the nonnegotiable 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 make connections 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 like 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 no need to push a false narrative or front, which is never a good idea. 

7. Relationships > transactions.

The world has become overly transactional, especially the business community. (The agency world is even worse, in fact, 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 damages all aspects of service, product development, morale, and, of course, 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. 


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