Interested in starting your own entrepreneurial journey in business development but unsure what to expect? Then read up on our interview with Matthew McKeown, CEO of Anchor Leg, located in Lynchburg, VA, USA.

What's your business, and who are your customers?

Anchor Leg is a company dedicated to helping technical founders without a sales background build stellar sales teams. We provide US-based sales teams along with a comprehensive 70-100 page sales playbook, ensuring your organization can successfully replicate our expert strategies. Our unique approach allows direct access to sales reps from day one, enabling you to handpick top talent and integrate them in-house. Plus, we grant you the playbook's intellectual property rights. Our method effectively extends a sales rep's tenure with your company from the US average of 14-16 months to 20-28 months, fostering stronger consistency and brand loyalty. We have clients in software, service, and the energy industry.

Tell us about yourself

I'm a top-performing sales rep and leader with experience across various industries. When COVID-19 hit, I saw a chance to pioneer remote sales solutions and seized the opportunity in October 2020. Today, our company has successfully booked hundreds of demos and generated millions in revenue for our clients, all remotely. My motivation stems from two sources: first, helping entrepreneurs realize their dreams by teaching them how to sell and building their sales teams. Second, on a deeply personal level, I lost my 15-year-old son to suicide in 2020. This inspired me to create the "It Is Worth Living" scholarship at Clemson University in his honor, awarded to a walk-on football player. Anchor Leg symbolizes both our commitment to being a vital part of our client's sales organizations and my dedication to carrying my son's legacy forward.

What's your biggest accomplishment as a business owner?

Selecting just one accomplishment is difficult, but I'd say my greatest achievement in the past three years has been finding five core individuals who wholeheartedly believe in Anchor Leg's vision. Their daily challenges and support have propelled us to new heights. Without this exceptional team, our current success wouldn't have been possible. The entrepreneurial journey is incredibly challenging, and having these dedicated team members by my side has been invaluable. Their unwavering commitment has transformed our aspirations into a thriving reality, and I am deeply appreciative.

What's one of the hardest things that comes with being a business owner?

One of the most complex aspects of being a business owner is recognizing that you can't do it alone. While many people understand this, the true challenge lies in trusting your team to make great decisions and supporting them even when they stumble. Your business's growth is directly proportional to the trust you place in those around you. Therefore, it's crucial to surround yourself with individuals who challenge you to rise above setbacks and encourage the same resilience in return. This mutual support and trust form the cornerstone of a thriving business.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

  1. Build a strong support network by surrounding yourself with people who believe in your vision and challenge you to succeed, especially during tough times.
  2. Trust your leaders! Remember that everyone makes mistakes, including you. Recognize their value and the reasons you brought them on board.
  3. Stay adaptable, and don't become too attached to your business model. Be prepared to pivot as needed. Take inspiration from companies like Outreach, which transformed from an HR solution to a multi-billion-dollar sales enablement enterprise after listening to clients and embracing a new direction.

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

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