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The Benefits of Startup Coaching: From Sales to Scaling and Everything in Between

Updated: Oct 28




“I’ve always been a self-taught person,” explains Trevor Rappleye, founder and CEO of Corporate Filming, a national digital media company specializing in videography and online content. Started in 2000, Rappleye’s journey reached a fork in the road when his founding partner left the team.


“He was the business side, the marketing and sales guy,” Rappleye remembers. When the partner left, he had two options: learn the skills himself, or close the company for good. Rappleye chose the former.


Rappleye soon realized that reading and attending seminars can be helpful, but ultimately, he needed some advice about how to scale effectively. He needed a startup coach.


Let’s Make a Deal

Rappleye is the first to admit that coaching can feel like a luxury, even when he finds it to be a necessity nowadays; “It is going to cost some money, but it is worth it. Develop yourself and your business will thrive.”


When Rappleye first met the startup coach he still works with today, the price tag made him balk. Instead of walking away from something he really needed, Rappleye was transparent with his coach about budget, and expectations. “At first, I think I paid him like $100 a month. It was for one phone call, but it was so cool to have just that hour of outside help because no one else was telling me I was wrong.”


Looking back, Rappleye can see those early days with his coach were important. “I would honestly say to someone who’s on the fence about paying for a business coach, it’s worth paying yourself less in the short term to bring somebody in because you need that support.”


Scaling Made Simple

Rappleye initially loved having someone to confide in about the stresses of running his company that wasn’t someone within the company, but he also grew to appreciate the attainable goal-setting his startup coach had him work through.


“It started out so simple,” remembers Rappleye, “He just asked about how I was making sales calls. He suggested I start making 20 calls a day. Easy right?”


As he scaled with his coach, goals grew incrementally, and the relationship shifted. They stopped focusing as much on Rappleye’s ability to sell and market the company and started talking about growing the team. It was Rappleye’s coach who first suggested he start hiring. The coach walked him through the process, helping the founder pass on his knowledge to new hires as his responsibilities changed.


“There’s a quote I love; ‘If you chase two rabbits, you will catch none,” Rappleye says. Working with his startup coach keeps him focused on one rabbit, one attainable goal or mission, at a time.


Eye-Opening Coaching Insights

Rappleye credits his startup coach for helping him think more big picture about his company, instead of day to day. Before coaching, the founder oftentimes spent days in the weeds, working on scheduling or answering emails. At the time, it felt productive, even necessary, but after working with his startup coach, Rappleye realized his own actions were limiting the company’s scale.


“It’s about getting down to the root of it and asking the right questions. It’s the best thing you can do in leadership, let the person realize they have to do something different.”


Answering his coach’s questions led Rappleye to an ah-ha moment about his company’s growth. In some ways, working with a coach gave him permission to think bigger, hire more (when needed), and start focusing on growth instead of just day to day.


As Rappleye’s needs as a founder have changed, so too has his relationship with his coach. From solving the day to day struggles of an early-stage start-up to helping him grow his responsibilities, the partnership has been a valuable tool in helping Rappleye grow as a founder and CEO.


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