SEP Solo Episode: You Can’t Teach Entrepreneurship


solo -You Can't Teach Entrepreneurship


The Journey of Entrepreneurship

People often ask me if I studied writing or marketing in college. They assume that’s where I learned how to do what I do today. 

And while I did learn some valuable lessons in school and I’m grateful for those experiences. There was really only one class that directly taught me the skills that I could use and still use today in entrepreneurship, it was called The Foundry. 

I want to share with you the lessons I learned from The Foundry today.



Links and Resources Mentioned in this Episode

Selling with Story

Groove HQ



Jake Jorgovan


The Foundry – Creating an Entrepreneur 

In some respects, The Foundry was a business incubator but there were not venture capitalist Shark Tankers with funding to share or startup gurus sharing their secrets to new entrepreneur apprentices. The goal was not to create a successful business it was to create an entrepreneur. 


We celebrated failures as much as successes and we recognized failure as an integral part of building a business and building a good entrepreneur. If you weren’t failing you probably weren’t doing it right.


You see I believe and continue to believe that you can’t teach entrepreneurship like you can teach mathematics, spelling, or many basic classroom lessons. I believe the best way to learn entrepreneurship is on the front lines and alongside a community of other entrepreneurs who are on the front lines learning with you. 


If you commit to lifting up a community, sharing what you learn, and helping others solve the problems that everyone brings to the table, then everyone can learn, prosper, and grow together. 


The Foundry was a place for people who wanted to start a business, become entrepreneurs and support each other on their journey.


Teaching Entrepreneurship

Each Monday morning I met with a group of 20 students, a handful of professors, alumni of the program and some members of the entrepreneurship community. And each week I would come away with new lessons and motivation to work hard on my own projects. 


Instead of traditional lessons or homework we would set our own plans and goals for how to best grow our business in the grand scheme of things week by week. While it was far from a normal class it taught me and allowed me to teach myself some of the most foundational lessons that has defined me as an entrepreneur. 


Today, I’m going to share some of those lessons with you.


Integral Lessons on Becoming an Entrepreneur 

Lesson number one, live life deliberately. 

One of the most challenging lessons of The Foundry is also one of the simplest, know what you want and make progress towards it. 


At the start of the program we would fill out something called the MOKR which is an acronym that stands for Mission, Objectives, and Key Results. You create a mission and purpose for the next semester, not a business mission statement but a mission for how you want to use this semester and what do you want to see at the end of the semester. 


Then you get clear on a couple of objectives or goals you want to achieve to advance that mission. Finally, you list the key results relating to each of those objectives and you need to be able to check those off to know that you have completed the objective.


Sounds simple enough but most people aren’t in the habit of getting so clear on their goals or what they want in their life or their business. Sure we talk about things we want, we even think about things we want quite a lot, but rarely do we write it down and break it into a clear plan that is achievable and actionable. 


The Process of Creating Actionable and Measurable Goals for Your Business

In The Foundry a student would start by saying, “I want to test this idea for a business.” To support each other as a community we would challenge each other to get clearer on our goals until they were measurable and falsifiable. 


“How many potential customers would you need to speak to to test your service or how much revenue would you need to make to know if this was a successful test? How are you going to create your test? Who are you going to speak to?”.


Digging deeper to clarify that goal and making it one where you can measure your progress helped refine and crystallize your idea. 


That old statement, “I want to test this idea for a service business,” can transform into something clearer like, “I have an idea for a service I want to create.” I’ll put together a test offering and I will cold call 10 potential clients each week for a month. 


If I can get 15 clients in that first month then I’ll know I’ll have a workable business.


What Does a Clear Goal Look Like?

This isn’t just useful for business goals, making statements like, “I want to get in shape,” becomes, “I want to be able to bench press my own body weight so I’m going to go to the gym three times a week for the next three months while measuring my bench press weight at the end of each month to know my progress.” 


When you have this level of clarity on your goals and what you want to achieve in your business then you’ll be surprised at everything that you can accomplish.


The process of deciding what the most important things for you to do each week and every day it’s one of the most empowering practices that you have. It changes how you feel when you wake up in the morning and it gives you a greater sense of purpose. 


Solo You Can't Teach Entrepreneurship (1) You value your time more and you feel more in control of your life. Over time, day after day, week after week, you collect a growing list of proof that you can control your life. Make your own choices. And that you are making progress towards those goals. 


We often underestimate what’s possible to achieve in a year and only by taking consistent and deliberate action can we find out what we really can do with that time.


Lesson number two, transparency is your friend. 

Transparency is not only useful for sharing our experience with others but as a tool for self-reflection. 


A game we play in The Foundry is pushing our peers to set higher expectations on themselves. If we say we’re going to do something, we go big on what we set out to achieve and have a playful and curious attitude when failing to achieve them. 


Solo You Can't Teach Entrepreneurship (1)The Management Report – Understanding the Why

Once we had our big goals written down and planned out we would meet once a week to share the progress, the plans, and the problems we were facing in achieving those goals. 


We would write all of this in a simple one sheet document called the management report. We’d also include a little on our reasoning on why we made these plans or why this is a problem. This gives us a chance not only to understand what happened but the why behind it. 


Understanding the reasoning behind the action allows for a much deeper level of feedback from your peers.


These reports would be shared with the whole group and reviewed by the group before our weekly meetings. Everything we said we’d do and everything we actually ended up doing. 


Though most rise to the challenge and thrive as a result of this game sooner or later we are confronted by the fact that we fall short on our words and our plans. Being accountable and transparent to yourself and others was motivating in this case and it was also enlightening. 


A Lesson in Failures

Missing one of your plans for the week or a goal was not a failure but a lesson. 


Was the goal not as important as you thought? Did you overload yourself and try and do too much this week? 

You see, failure happens to everyone but most people try to cover their tracks and avoid these uncomfortable realizations.


Having our work and our plans written in management reports keeps us from the denial and rationalization that people typically experience with failure. Because we are accountable to ourselves and our community we ask the difficult questions to understand why we failed and what we can do instead next time. 


Confronting our shortcomings allows us to make real steps towards improving ourselves. It’s a painful process but if you want to be better it’s necessary. This is where the game comes in. Instead of lamenting on our failures we approach them with a playful and curious attitude. 


Failures Are Valuable Tools and Important to Success

We were able to examine what happened with a light heart and learn from it. Where most might turn away from their failures, the high expectations, playfulness, and transparency allow us to fail often and learn from it and make those failures valuable and powerful. There are many startups that understand the power of transparency on this level not only internally with their teams but externally.


Monthly Reporting in Action

In my time working with WP Curve our monthly reports reported on many of the things I shared. Such as the progress we were making, the plans we had for the future and how our content was doing. All of these topics were some of our most popular and effective articles on our site. 


Groove HQ, a customer service startup, embodies this transparency and honesty in their blog. They have used it as a tool to take their business to over 5 million a year in annual recurring revenue at the time of reading that article. Which is probably several years old by now so they’re probably much bigger and they’ve grown by building trust with their audience.


Buffer, a social media tool has the salaries of all their employees publicly displayed on their website. 


They also have lots of fun and interesting ways to share transparency as well like a Pinterest board dedicated to what the employees are reading at the moment. Doing this not only builds trust on the team, but allows the audience and the customers of Buffer to get a little bit of a peak behind the curtain at the people who are creating their projects. 


[bctt tweet=”Creating this personal human connection is one of the most powerful currencies that you can really develop with your audience and your followers. – Kyle Gray” username=”kylethegray”]


Jake Jorgovan, a recent podcast guest, credited this transparency and this currency “on his personal brand” as one of the biggest drivers of customers in his business. 


This level of transparency may seem uncomfortable at first but it can be a powerful tool for growth. It builds trust between you and your team. When they are clear on everything that is happening in the business. Your audience trusts you more because they know they are seeing the honest version of yourself.


Lesson number three, There is More to Entrepreneurship than a Successful Business

Many businesses were created in The Foundry and business is often a central topic for our discussions but The Foundry process teaches something more subtle and profound than just working on a business or project. 


It teaches a philosophy and approach that you can use to take control of your life, education, and your time. It helps you be more effective in your work but also in your relationships. 


We weren’t attached to specific business ideas of our participants or the success of the businesses themselves. We focused on creating better entrepreneurs. Good entrepreneurs can manage the balance of their lives and know how to cultivate their own personal health and relationships as well as their revenue. 


Though many students wanted to create some sort of business or startup with the potential for growth others chose smaller projects based on a passion of theirs that would fit in with their busy work or school schedule.


Revenue is easy to focus on but It is Not The Only Priority

It’s a simple number and it’s a good indicator for success but it’s not the only priority. We too often get caught up in the stories of billion dollar buy outs for Instagram or overnight successes. This becomes difficult to imagine other goals. 


Cassidy – A Story of Failure that Launched Success

My friend Cassidy’s story is an excellent example of that. Cassidy was a young snowboarder from Idaho. A skilled craftsmen and designer. He could build tiny houses, sell clothing, and design websites and graphics but he was also quite shy and unsure of himself. 


The first day of The Foundry, Cassidy found himself in a room of 30 people. He was so paralyzed with shyness that he did not introduce himself to anyone in that first meeting.


He joined The Foundry to build a print shop with his girlfriend. They set up their large printer and supplies in a coworking space where The Foundry met. His girlfriend handled the marketing and sales while he did the fulfillment and design. 


For him the thought of speaking in front of a group or calling up a customer to close a sale terrified him. After a few months, he separated with his girlfriend leaving him homeless, carless, and business partnerless sleeping in the cubicle he had built in the coworking space. He had no money saved and the only choice was to return to his home or make his business work. 


He slept on the floor each night underneath his desk and cooked most of his meals out of a small rice cooker. Without the help of his girlfriend, sales started to slow down and money became very, very tight. 


Cassidy continued to participate in the weekly meetings of The Foundry and built relationships with the entrepreneurs that worked in the coworking space. The friends and connections he made helped him overcome his fears and recover his business and his life.


He took a job as a pedicabber, which is a mix between a bike and a taxi, to bring in extra cash during the night hustling prints by day and pedestrians by night. 


With the support of the community of entrepreneurs he met through The Foundry he kept working hard despite the impossibly difficult situation he faced. He learned how to speak with his customers, close a sale, and promote his business. He also sharpened his sales skills further night by night with pedicabbing. There’s not very much room for shyness when you need to convince people to hop in your pedicab and have you drive them around town. 


Just barely a year later Cassidy was in front of a large group of entrepreneurs giving a presentation on his business. He was explaining his target market, how he worked with his customers, and some of the challenges he faced. 


Totally transformed from how he was a year earlier he was energetic, enthusiastic, and charismatic.


Shortly after Cassidy found an apartment he could afford with the new earnings from his business and within a year of joining The Foundry, Cassidy had reinvented himself. 


But the best part of his story was just beginning because Cassidy wanted to travel and inspire others to follow their dreams through photography. He had ambitions to bike through New Zealand, Australia, and Southeast Asia. Hauling people on a pedicab night by night had strengthened him physically for the challenge. The months spent living in a cubicle taught him to live simply and he was quickly able to save for his journey. 


Using the sales skills he developed with his print business he found sponsors and began to build interest in his new project. This evolved into a two year bike trip around New Zealand practicing photography, taking design jobs online and odd jobs on the road to continue to finance his adventures. 


He found the confidence and skills to control the direction of his life, follow his passions and his dream. He learned to be open to the kindness, coaching, and the feedback of others. While having the courage to put himself in uncertain and risky situations. Far from being a seven figure business or $1 billion exit Cassidy found his own definition of entrepreneurship and Cassidy discovered what he loved to do and found his own way to do it.


And those are the three lessons that The Foundry taught me. 

You don’t have to attend a university or be accepted into a fancy business accelerator to experience the benefits that I described in the foundry. You can build your own foundry by creating a community of peers, getting everybody clear on their goals and what they want to achieve. Then holding each other accountable week by week to make measurable progress towards those goals. Encouraging creativity and curiousness and growing from failure.


And those are my lessons from The Foundry and why I believe you can’t teach entrepreneurship. Thank you so much for listening and if you enjoyed this episode or the other interviews on this show please leave us a review on iTunes. 


Thank you so much,



Thanks for listening to the Story Engine Podcast. Be sure to check out the show notes and resources mentioned on this episode and every other episode at If you’re looking to learn more about how to use storytelling to grow your business, then check out my new book, Selling With Story: How to Use Storytelling to Become an Authority, Boost Sales, and Win the Hearts and Minds of Your Audience. This book will equip you with actionable strategies and templates to help you share your unique value and build trust in presentations, sales, and conversations, both online and offline. Learn more at Thanks for listening, and I’ll see you next time.