Entrepreneur to Investor: Jason Mackey’s Personal Journey from Serial Entrepreneur to Emerging Venture Capitalist
Jason Mackey, a serial entrepreneur, and emerging venture capitalist, has a proven track record of fostering successful businesses in the United States and the United Kingdom. Through his various ventures, including CXOHQ, Venturitas Venture Advisory, and Occam Strategy Group he has imparted growth strategies and fundraising insights to over 200 established and burgeoning ventures across dozens of industries worldwide. As a Co-founder and General Partner at Athenian Capital, Mr. Mackey is raising a $50 million early-stage fund to invest in diverse teams, building the next generation of iconic companies with clear pathways to long-term profitability. Beyond Athenian, Mr. Mackey is President and CEO of the Economics Rights Council, a Boston-based non-profit working to guarantee economic security for all Americans. In 2022, he ran for State Representative of the 27th Middlesex District in Massachusetts on a pragmatic platform of diversity, inclusion and the promotion of economic opportunity.
How did you break into tech investing?
Through the back window, so to speak. I started out as an entrepreneur in my dorm at Northeastern and had the privilege of co-founding several ventures spanning a wide array of sectors since then. This hands-on experience gave me a front-row seat to the rollercoaster ride that every startup undergoes. I developed a deep appreciation for the challenges startups face, the immense potential of emerging technologies, and the transformative power of a robust strategy.
Arguably, the best tech investors are the ones with the experience of founding a company and building something from nothing. And so, with my entrepreneurial background as the centerpiece of my resume, I started dipping my toes into angel investing. Each investment, each startup story added a new layer to my understanding of the intricate landscape of tech investing, igniting a passion that eventually paved my way to raising my first venture fund.
Co-founding Athenian Capital was a significant milestone. Today, as a General Partner, I hope to be not just a spectator but a part of the game — shaping investment strategies, supporting innovations, and helping redefine the technology landscape.
What is it that excites you about investing?
Investing for me is akin to diving into an ocean of possibilities. There’s an exhilarating thrill in discovering and backing what could become the next Salesforce or Zoom, the next technology that could revolutionize our world. The journey of walking alongside entrepreneurs, supporting their dreams, and helping them beat the odds is incredibly rewarding. And the dynamic nature of economics, the ebb and flow of consumer trends, keep me intellectually stimulated, much like a never-ending game of chess.
What has been your biggest challenge when it comes to finding the “right deals”?
Imagine you’re at one of the best whiskey bars in Manhattan with over a thousand bourbons to choose from, and you can only pick one. That’s the challenge we often face in the venture capital world. Identifying startups that resonate with our investment philosophy amidst a sea of promising ventures can be quite a task. Evaluating early-stage companies’ potential with often limited data is like piecing together a jigsaw puzzle without the complete picture; but such is the nature of early stage investing.
What major trends do you expect to see in technology innovation over the next 5 years that excites you?
As I peer into my crystal ball, a few trends immediately grab my interest. Artificial intelligence and machine learning, for one, will become our daily companions, reinventing how we interact with healthcare, automation, and more. Biotechnology is poised for exciting breakthroughs, with gene editing and personalized medicine potentially rewriting the rules of healthcare. The advent of quantum computing holds the promise to unravel mysteries that have been out of reach for millennia. Not to mention the rise and rapid adoption of both renewable and sustainable tech paints a promising picture of a bright tomorrow. It’s these changes and revolutions on the horizon that make tech investing so exhilarating!
If you had to share, “words of wisdom,” with a Founder who’s about to start their own startup, what would they be?
I’ve founded a number of different companies, each to varying degrees of success, but I loved them all. As you’re just starting out on your entrepreneurial career, remember that it’s the journey, not just the destination, that holds immense value. Prioritize your customers, for they are your north star. Stay agile, adapt to market dynamics, and keep your finger on the pulse of consumer trends. Build a team as diverse as the world you aim to impact. Let resilience be your armor against setbacks. Seek guidance from mentors, and never forget to savor and enjoy this exciting rollercoaster ride called entrepreneurship! Also, don’t forget to treat your sales and marketing teams with respect because without them, your company is nothing.
How can our readers follow you on social media?
I’m trying to be more active on LinkedIn and Twitter these days, and you can find me on most platforms at “MackeyJasonD”. I also recently launched a blog, www.mackey.vc, where you can read more about my love of investing, entrepreneurship, and my occasional ramblings on politics and cars.
This was very insightful. Thank you so much for joining us!
