Coaching Through the Founder Lens

April 8, 2024

It’s a well-known fact, being a founder is hard. You’re navigating the unknown, and often the only people who truly understand what you’re experiencing are other Founders. Let’s face it,starting a company is scary. And then when you do, there are expectations and assumptions of what it will be like, and how you are going to change the world.

- We will build this amazing product and everyone will buy it

- This new way of solving a big problem is going to change the industry

- We are going to raise millions and then IPO

In the rollercoaster ride that is “startup life”, founders put everything on the line to make their vision a reality. Bootstrapping the way forward, finding ways to make each dollar count to avoid that dreaded ‘running out of runway’ situation. On the ‘up’ side: landing your first customer, hiring your first employee willing to take the leap, winning a pitch competition or getting a term sheet.

All that to say, the journey can be very lonely. Sometimes as founders we don’t know what we don’t know, and we take any support and advice that comes our way. Over time, we learn how to better navigate the advice. Ultimately, as a founder you are the biggest investor in your company, and you want to make sure you’re focused on meaningful progress (as opposed to just being ‘busy’).

It’s a point of pride for our team that all of the Startup Coaches at Propel are founders, as well as most others on our team. We’ve been there.We can empathize with the rollercoaster, and help distill the inundation and conflict of ‘mentor whiplash’ - the overabundance of advice and decisions to be made.

We offer a few examples of difficult decisions and key insights from our coaches from their experiences as founders:

Coach Kyle was owner and co-founder of a restaurant that expanded to five locations. One of his most difficult decisions was to start in the first place. He knew he was taking a large risk in moving into a new and well-saturated industry, but he validated the customer opportunity and took the plunge. When it came to his insights and learnings, for him it was learning to understand the KPIs of his business and how they influenced the operation. He became obsessed with operational planning and he learned to time everything to the second. If he knew how long something would take, he knew his baseline, and knew on the fly if things were fast or slow, which was particularly important given that about 50% of the business happened within a 90-minute window. Understanding the KPIs helped the planning, which helped with customer satisfaction and retention. His key takeaway - look to build more customer centric KPIs as well as operational ones.


Angela, our Director of Operations ran a retail crafting business. For her, the most difficult decision she made was admitting when it was time to close down the business and informing the staff who had supported her know that the business wouldn’t continue. Upon reflection, the number one thing she learned is that failure doesn't define you. Becoming an entrepreneur was scary and involved risk, but she loved it. It took her a long time to reconcile that the failure of the business wasn't a direct result of anything that she did and that sometimes circumstances and timing play a huge role in business success.


For me, I realized early in my business that I had not done enough customer discovery, and had over-built our product. More customer validation before building product would have made the path to customer value and revenue, as well as fundraising much smoother. The second difficult experience was communicating the devastating news that our Seed round had fallen apart, five days before cash was going to be landing in the bank account, which meant we were running out of cash entirely. I had been given conflicting advice as to whether to tell the team immediately or not. Some said I should wait until the last day. Instead I chose to face the news head on. While I was half expecting some of the team to walk away, they asked to stay, which I am eternally grateful for. The key learning for me was how important it was as a founder and leader to manage communication with respect and integrity, be it positive or negative (and don’t celebrate before cash is in the bank).


For Coach Richard, who has been a serial entrepreneur, his challenges involved people. Richard had a key team member who he had recruited and worked for him for several years, but then resigned abruptly. Richard didn't see it coming and it took a few weeks to recover, personally and professionally. Another difficult experience was getting fired as the CEO! It happened twice - the first one was done respectfully, the second one was done unprofessionally. But indeed, both character building and intense learning experience. The number one thing Richard has learned is that leading an early stage startup is going to be more difficult and more personally challenging than one can imagine. Be prepared for a lot of setbacks. But if you're willing to go through the "leadership pain", the growth will be significant, taking your leadership skills to a new level.


As Startup Coaches, we draw on our experiences to better support our founders. We can empathize with how hard the road is, and that there is no one-size-fits-all approach to validating, pivoting, growing or scaling a business. As founders, and as coaches, we continuously check for blind spots, and test assumptions. As Chris Neumann recently posted, there is a difference between ‘experience and expertise’. While both are important, experience and expertise are not interchangeable.