I used to be stubborn about where I put my money. Real estate seemed like the perfect complement to my marketing agency—a stable asset balancing the volatility of my cash flow business. I had my plan and wasn’t interested in deviating from it.
Then a friend approached me about investing in his startup. I immediately shut him down: “I’m not investing in startups.” But his response caught me off guard. He wasn’t asking if I wanted to invest—he was telling me I was going to invest, even if it was just a small check.
Reluctantly, I agreed. That company is now worth between 3 to 5 billion dollars.
That moment was a wake-up call. My stubborn adherence to my investment strategy had nearly cost me an incredible opportunity. I realized I needed to take a more open approach to investing, especially in areas that could impact my core business.
Embracing Disruption Instead of Fighting It
This experience completely shifted my investment philosophy. Instead of avoiding tech companies that might disrupt my marketing agency, I decided to become a part of them. Why fight the tide of innovation when you can ride the wave?
Since that pivotal moment, we’ve invested in nearly 100 marketing tech and ecommerce tech companies. These aren’t random investments—they’re strategic positions in tools, software, and innovations that we actually use in our business.
My reasoning is simple:
- The marketing landscape is constantly changing
- New technologies will inevitably disrupt traditional marketing approaches
- Being an owner in disruptive companies gives you insight and influence
- Financial upside comes from both your core business and your investments
This approach has transformed how I view potential threats to my business model. Instead of seeing new marketing technologies as competition, I see them as opportunities for partnership and growth.
The Power of Strategic Investing
I’d rather be a partner and owner in the companies that will disrupt what I do than a competitor trying to hold onto outdated methods. The future belongs to those who adapt, not those who resist change.
This mindset shift has benefits beyond just financial returns:
- Early access to new technologies that can benefit my agency
- Relationships with founders who are shaping the future of marketing
- A hedge against disruption in my core business
- The ability to help guide these companies in directions that create mutual benefit
- A diversified revenue stream beyond service-based income
By investing in the tools that my agency uses, I’ve created a virtuous cycle. We help these companies grow through our usage and feedback, and their success benefits us both as users and as investors.
Winning With Change, Not Against It
The marketing world will continue to evolve. Client needs will shift. New technologies will emerge that change how we deliver value. But instead of viewing these changes as threats, I’ve chosen to fully embed myself with them.
This doesn’t mean abandoning my core business. It means recognizing that what we do and how we do it will inevitably change. By positioning myself as both a service provider and an investor in marketing technology, I’ve created multiple paths to success.
The lesson here isn’t just about investing—it’s about mindset. When faced with industry disruption, you can fight it or find ways to win with it. I’ve chosen the latter, and that decision has opened doors I never would have seen if I’d remained stubborn about my original plan.
So the next time someone tells you to invest in something outside your comfort zone, consider it carefully. Your initial resistance might be keeping you from an opportunity that could transform your business and your future. Sometimes the best investments aren’t the ones you seek out, but the ones that find you.
Frequently Asked Questions
Q: How do you decide which tech companies to invest in?
I focus on marketing tech and ecommerce tech companies that create tools and software we actually use or might use in our agency. This gives me both practical insight into their value and a strategic advantage if they succeed in changing the industry.
Q: Isn’t there a conflict of interest in investing in companies whose services you use?
Rather than a conflict, I see it as alignment. We become better customers because we have skin in the game, and we become better investors because we understand the product from a user perspective. This creates a win-win relationship.
Q: What was the biggest challenge in shifting from real estate to tech investing?
Overcoming my own stubbornness was the biggest hurdle. Real estate felt safe and predictable, while tech startups seemed volatile. Learning to evaluate tech companies required developing new skills and embracing uncertainty in ways real estate investing doesn’t demand.
Q: How has being an investor changed how you run your marketing agency?
It’s made me more forward-thinking and adaptable. I’m constantly looking at how new technologies might change our industry, and instead of resisting those changes, I’m positioning my agency to evolve alongside them or even ahead of them.
Q: What advice would you give to other business owners facing disruption in their industry?
Don’t fight the inevitable changes in your industry. Look for ways to participate in and benefit from disruption rather than resisting it. This might mean investing in competitors, forming strategic partnerships, or adapting your business model to complement new technologies rather than competing with them.
