10 Lessons I’ve Learned From Running Multiple Startups and Ventures

“The best business school is running a business. The smartest entrepreneurs learn, pivot, and invest from experience, not just theory.”

Retoro Capital Investments

Over the years, I’ve launched, managed, and scaled several businesses. Each venture has taught me valuable lessons, only some learned the hard way! The following insights aren’t revolutionary: in many cases after my real-world realization I would then find mainstream entrepreneurial wisdom already published about the same lessons. As so many of our passive investors are also business owners themselves, we learn a lot from one another that we can apply in our respective ventures. Hopefully you'll find value here as well, and if you do, we'd love to talk about investing together.

1. Stop wasting time delivering budget services.

When I first started freelancing as a graphic designer, I made the classic mistake of undercharging for my work. I thought offering budget-friendly services would make me competitive, but it just left me overworked and undervalued. The truth hit me when I realized I was sacrificing time with family to crank out projects for clients who didn’t appreciate the effort. Once I raised my rates, everything changed: I started attracting higher-quality clients who respected my expertise and were happy to pay for it. It’s a lesson I wish I’d learned sooner. (Episode #15)

"The only way to serve the bottom of the market is to be the cheapest, and the only way to be the cheapest is to have the largest volume.", Alex Hormozi, $100M Offers

2. Don’t price based on competitors, price based on yourself.

This may sound counter intuitive to not pay attention to your competitors. I'm not saying to be unaware, but to become more honestly aware of yourself and your own business.

If I’m dreading a project or feel like it’s not worth my time, I know my price is too low. On the flip side, if I’m overly anxious about delivering value, I’ve probably priced too high. Once I started adjusting my prices based partially on how I felt about the client or project, rather than to match competitors, I not only earned more but also enjoyed my work more.

"Expertise is the only valid basis for differentiating ourselves from the competition. Not personality. Not process. Not price.", Blair Enns, Pricing Creativity

3. There are bad customers, but you can learn to spot them.

Not every customer is worth your time. I learned this one the hard way in my real estate photography business when I ignored red flags from a client who was late to every meeting and constantly complained about costs. Once the complaints started trickling then piling in, that taught me to trust my instincts and pay close attention to how clients communicate during initial conversations, both verbally and non verbals. There's a time for openness without judgment, and there are times when it saves me headaches in the long run.

"Nonverbal behaviors comprise approximately 60 to 65 percent of all interpersonal communication...", Joe Navarro, What Every BODY is Saying

4. Communication trumps all.

One of my biggest mistakes working with vendors in my real estate business was to not ask clarifying questions to ensure rather than assume people understood my expectations. I’ve learned to overcommunicate, even to the point of getting teased about it, whether it’s with clients, employees, or contractors. Clear expectations lead to better results.

"People who are skilled at dialogue do their best to make it safe for everyone to add their meaning to the shared pool...The Pool of Shared Meaning is the birthplace of synergy.", Kerry Patterson, Crucial Conversations

5. Scale smart.

For a long time, I resisted scaling my multifamily real estate business because I was focused more on early retirement and didn't want to lock myself into any long-term commitments. After we hit our level-one retirement goal and no longer had to work, we still wanted to be involved in scaling a business both to grow our own wealth and gain fulfillment helping others to grow theirs. We took a backpacking sabbatical for three months after retirement to take time to think ahead about what that would look like, and what type of business would be the best fit.

"Goals without routines are wishes; routines without goals are aimless. The most successful business leaders have a clear vision and the disciplines (routines) to make it a reality.", Verne Harnish, Scaling Up

6. Love what you do, or someone who does will outwork you.

Start with what you love, but don't end there! I am a person with 1,000 hobbies: I'm a high "open" personality type and am interested in almost everything (sorry, skiing, I still hate you). I looked at all the things I enjoyed doing and chose the one that had the most income potential. I knew I could be happy doing a lot of things, but I chose which of those things had the most value in the marketplace. Loving what I do helping my family and other families has made a huge difference in both my motivation and my results by helping give me and edge by working hard with enthusiasm.

"Skills are cheap. Passion is priceless. You need to love what you do because if you don't, someone else who does will outwork you.", Gary Vaynerchuk, Crush It!

7. You don’t need the next big idea, you just need to execute.

Whenever I start a new business, I remember the familiar quote from Jeff Bezos about asking what doesn't change. Or the story in Millionaire Fastlane MJ DeMarco when considering starting a limousine service feeling overwhelmed how many other companies were already in his area when his girlfriend told him he didn't have to be the first or the only, he just had to be the best. Like him, we just focused on our strengths to deliver value from there.

"Replicate before you innovate.", Alex Hormozi, $100M Leads

8. You don’t have to be the only one, you just do it better.

As a former photography and graphic design freelancer, I knew I wasn’t the only designer in town. What set me apart was my professionalism, something creatives are not usually known for. I made sure to meet deadlines, communicate effectively, and deliver exactly what the client asked for. That level of service earned me referrals and repeat business. Sometimes, simply being reliable is enough to beat the competition.

“A market is never saturated with a good product ,but it is very quickly saturated with a bad one. Henry Ford”

9. Build as if you intend to exit, even if you don’t.

I’ve never sold a business, but learning how to build one that’s sellable transformed the way I work. For example, in my real estate business, I systemized everything: automated rent collection, documented processes, even branding from the start. These changes made the business easier to manage and more enjoyable to run. Whether or not you plan to sell, building as if you will forces you to prioritize efficiency and professionalism.

"You need to build your business with that end in mind and then build it on the infrastructure so it is sustainable and scalable.", Michelle Seiler-Tucker, Exit Rich

10. I’m not an entrepreneur: I’m an investor.

For years, I identified as an entrepreneur, but I’ve come to realize that’s not really who I am. What I love is building businesses that generate cash flow and then investing that money into passive income streams. This mindset shift was liberating. I no longer feel the need to hustle endlessly. Instead, I focus on what I’m good at, pile up cash, and invest in assets like real estate, stocks, and small businesses. For me, entrepreneurship is a means to an end, and I give my businesses a deadline now.

"The goal is not to work hard for money, but to make your money work hard for you by owning assets that generate cash flow.", Robert Kiyosaki, Cashflow Quadrant

11. Bonus: Learn to play the tax game that the wealthy create the rules for.

There's a blueprint on how to build wealth found in the United States tax code. What activities are incentivized? Those can become an extra stream of income to you in your business and personally.

Our preference is the real estate professional status, spending over 50% of our time in a real estate business as owners/managers on qualifying activities, 750 hours a year minimum: this allows us to use unlimited depreciation from properties we own or invest in to offset our active/ordinary income. A business is not passive: we prefer to earn our base level income passively to free us up to think about how to make the most of our time in our business.

“If you don’t understand taxes, you’ll never be truly wealthy. Owning a small business is the best tax deal in America.”, Codie Sanchez, Contrarian Thinker

Final Thoughts

These lessons have shaped how I approach business and even life. I hope they serve as guideposts to help you avoid some of the mistakes I’ve made and find more joy and success in your own ventures. Since the best business school is actually running a business, what lessons have you learned on your journey? Let’s continue the conversation in the comments and on a call at partnerwithrci.com to see if we are a good fit to do business investing together.