Reflecting back on a Decade of Entrepreneurship

February 1st, 2017

I received an incredible amount of messages this last week congratulating me on Matchbook’s anniversary. LinkedIn provides great PR for work anniversaries, but what touched me most was the gratitude coming from people who said I had inspired them as an entrepreneur.

I founded Matchbook 10 years ago. It is great business that provides strategic sourcing and procurement services to an expanding number of fast growing companies. It has given me the opportunity to work across a hundred different organizations and gain deep industry insight. Over the past couple of years, I have been able to attract a talented and experienced team to carry the torch while 150% of my time and energy is spent building and growing tealbook.

As I enter my second decade of entrepreneurship, I can’t help thinking how much I have grown and learned. I know that being an entrepreneur is not for everyone. It is risky, scary, and a constant roller coaster. But I wouldn’t want it any other way… For me, it is freedom, passion, and perpetual change that allows me to devote myself so completely to building my vision. Creating something from nothing and being so directly accountable for its success is enormously gratifying.

Growing a service company was no walk in the park. It required putting myself out there and acquiring new clients on my own until I was finally able to build a team. The work depended on my ability to manage processes and leverage my deep industry experience. It has been a gift that has allowed me to become somewhat of an industry expert and uncover an unmet need in supplier intelligence and discovery. It led me to tealbook.

Building a technology company is a completely different beast. It has tested every inch of me and has elevated me from entrepreneur to CEO. It constantly pushes me to step outside of my comfort zone in a giant jigsaw puzzle that has required me to lean on an army of people to reach each critical milestone. In this new phase of my journey, I am excited to be growing our team and working with them, our customers, and suppliers to accelerate our growth and reach new heights.

For anyone in the early stages of an entrepreneurial journey or thinking about taking the leap of faith, here are some of my key learnings which I hope can help:

1) Naiveté is a gift. If I had known how hard it was going to be to build technology from scratch, I could have been persuaded not to do it. Not knowing allowed me to take the plunge and put the pieces in motion. Once you’re in it, the only direction is forward and my appetite for learning is insatiable.

2) Don’t start with a plan. This goes against everything you’ll read in business books, but it helped me to get started without finding excuses. The business plan would have been hard to develop without truly understanding the market opportunity. For this, I needed real insight from my extended network and they were much more inclined to help knowing that I was truly invested. The plan evolved and became much clearer as the business grew.

3) Surround yourself quickly with smart people that complement your skills. Recognizing your weaknesses and skills early on and complementing them with experienced people is critical to survival. You need to learn quickly how to sell your vision and find people that can get really excited about it. When someone doesn’t buy in or is not aligned on your vision, don’t wait and see. Move on. You will both be better for it.

4) Step outside of your comfort zone every day. You’ve stepped outside of the ‘known’ by starting the company, but in order for it to be a success you have to continue to push yourself. You should have a ‘feeling scared’ moment every single day. 🙂

5) Listen to your customers and industry experts. Bringing in clients and industry experts early into our journey allowed us to learn the real market opportunity and build strong advocates for tealbook. They have been an integral part of building our platform so it best meets their needs. As the product evolves, it is important to continue asking questions and welcoming criticism. It is the only way you can truly improve and deliver a better product and experience.

6) Don’t give up. Being an entrepreneur is the loneliest job in the world. In the early stages, everything depends on you and you will doubt yourself a million times. Surround yourself with positive people that believe in your vision. Remember that you did this for a reason that was strong enough to make you choose this path and take this leap of faith.

I invite other entrepreneurs and founders to add to this list and hopefully inspire many more people to start their own journey.

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