Episode 050: Sixteen Years Making Someone Else Win Till He Discovered Himself with Derek Fredrickson
Episode Summary
Derek Fredrickson was very good at making other people win. That was his gift, his lane, and for sixteen years his entire identity. Wall Street first, Deutsche Bank, Lehman, UBS, running project management and doing what analytical, disciplined, systems-minded people do well inside a machine that rewards exactly those traits. Then the train ride that changed everything. He looked across at a man in his mid-seventies on the five forty-one commuter rail from Connecticut to New York, exhausted, and thought: is that who I want to become?
He did not run. He made a calculated decision, the only kind he makes, and left Wall Street to join his wife Fabienne's coaching business. He worked his way up from the mailroom. He paid himself the same salary from day one so the ego had no ammunition. He became the string to her kite, the one who landed the plane, who finished what she started, who took a vision and built the execution from A to Z. Then he helped scale it to multiple seven figures. Then he did the same fractionally for other founders. For sixteen years he was the best number two in the room and he was proud of that.
What he did not know until he stepped out was how completely he had wired his identity into someone else's vision. In 2024, he made another calculated decision, the kind that take him time and thought and spreadsheets and pros and cons lists, and launched The COO Solution, a fractional COO and second-in-command placement firm operating from Paris, France, where he lives with Fabienne and their three children. Twenty-five people on the team. Multiple seven figures. A ten year vision he looks at constantly. A weekly metrics review he does every single Monday without exception. And a mantra from his wife that has carried him through every low: no small children will be harmed.
This is episode fifty of the Grit Factor. It is the right episode for the milestone because Derek's story is not about the founder. It is about the person behind the founder who finally stepped in front of their own vision for the first time. This episode is for every operator, every second in command, every engine behind someone else's dream, who has quietly wondered if there is a dream of their own waiting.
In This Episode, You'll Discover:
- The five forty-one commuter train from Connecticut to New York, the man in his mid-seventies who looked exhausted across the aisle, and the question that moment planted in Derek that sent him from Wall Street into entrepreneurship two years later
- What it cost his ego to go from being a Wall Street professional to working in his wife's coaching business, why he told friends he worked with her not for her, and how they structured equal pay from day one to protect the power dynamic
- The Strengthsfinder and Kolbe assessments Derek uses with every client and why he believes knowing how you are wired to take action is more important than any business strategy you could deploy
- The four quadrant framework Derek uses with founders, unique brilliance, excellence, competent, and incompetent, and why most entrepreneurs waste the majority of their time in the bottom two quadrants doing work that someone else should own
- What the mastermind dinner moment taught Derek about not needing to be the big idea generator, how the mastermind owner reframed his role to the table, and why that validation changed how Derek shows up in every room since
- How Derek made the identity shift from number two to CEO, why it took him years of deliberate thought rather than a spontaneous leap, and what the difference is between a think talker and a talk thinker
- The weekly metrics review Derek runs every Monday without exception, how he structures it across marketing, sales, operations, and finance, and why asking why when things are on track is just as important as asking why when they are off
- The ten thirty-one framework Derek uses for himself and every client, ten year vision, three year plan, and one year picture, and why starting with the end in mind and reverse engineering is the only system that has ever worked for him
Key Takeaways:
- The Drunk Monkey Is the Enemy. Derek's wife's phrase for the voice on your shoulder that says who are you, why would you think you can do this, you are not qualified. Every high performer has one. The volume varies. The solution is always the same. Plug back into your why. Look at the ten year vision. Do not let the drunk monkey steer.
- You Cannot Scale Bob. You Can Scale Structure. If the knowledge of how your business runs lives inside one person's head, you have not built a company. You have built a dependency. Get everything out of Bob's head and into runbooks, playbooks, SOPs, checklists, and project management systems. Then Bob can be in the rainmaker lane. The structure runs everything else.
- Live in Your Lane. Stop Apologizing for It. Derek is not a born entrepreneur in the classic visionary sense. He knows it. He owned it in a mastermind dinner in front of ten founders. And the response from the room was that without someone wired like Derek, every big idea discussed over dinner dies on the table. Know what your lane is. Be unapologetically in it. That is where you create the most value.
- Numbers Tell the Story. Feelings Estimate It. Derek's weekly metrics review is not optional. It is every Monday, every week, no exceptions. Because gut checks are necessary but insufficient. The question is not just are we on track or off track. It is why. The why reveals the issue underneath the problem. You do not want to fix problems. You want to solve the issue causing them.
- One Plus One Equals Three When You Each Know Your Lane. Derek and Fabienne built a multiple seven figure business by being in completely different lanes simultaneously. She created. He executed. She started. He finished. She ideated. He built the framework. The moment they blurred the lines, there was friction. The moment they respected each lane, the business compounded.
- Wear Two Hats. Never Combine Them. Working with your spouse requires deliberate separation of the professional and personal relationship. Derek learned the hard way that bringing a client email into a quiet evening with a glass of wine is not a small infraction. It blurs the lines and burns both sides. The husband hat and the work hat do not co-exist. Put one away before you pick up the other.
- Start With the End in Mind. Then Reverse Engineer. Every business Derek has helped scale and every goal he has set for himself started with a clear ten year picture. Not a vague aspiration. A specific, number-driven, impact-defined vision. Then three years. Then one year. The how figures itself out when the what is specific enough and the why is strong enough.
- No Small Children Will Be Harmed. This is the mantra that carries Derek through the lowest moments. Not a scripture. Not a framework. A perspective check. Nobody is bleeding. There is a roof over the heads. The problem, whatever it is, is solvable. Take a nap. Go for a walk. Get back to a positive state. The world is not ending. It just feels like it is.
Timestamps:
- [00:00] Karl introduces Derek Fredrickson on the milestone episode fifty: Wall Street to Paris, sixteen years as a number two, now building The COO Solution with a team of twenty-five
- [03:00] The five forty-one train, the exhausted man across the aisle, and the moment Derek asked himself if that was who he wanted to become
- [07:00] Leaving Wall Street in 2008 to join his wife's coaching business, the ego cost of saying he worked with her not for her, and the equal pay decision that protected the dynamic
- [12:00] Karl's ad break: The Grit Code Exposed at https://gritcodeexposed.com
- [13:00] Being a beginner in his wife's business, starting in the mailroom, and using Strengthsfinder and Kolbe to identify his lane instead of trying to be someone else
- [18:00] The string to the kite analogy: what it looks like when a creator and an executor are fully in their respective lanes
- [23:00] How the working marriage dynamic actually functioned: the conflicts in the beginning, the evolution, and the two hat rule that finally made it sustainable
- [28:00] The mastermind dinner: teetering on imposter syndrome in a room full of visionaries and the owner's reframe that changed everything
- [33:00] The identity shift from number two to CEO: why it took years of deliberate thought, what the difference between think talkers and talk thinkers means in practice
- [38:00] Karl's ad break: The Grit Code Exposed at https://gritcodeexposed.com
- [39:00] The four quadrant framework: unique brilliance, excellence, competent, incompetent, and why most founders live in the bottom two
- [45:00] Delegating, automating, systematizing, and outsourcing: the framework for getting the founder back into the top quadrants
- [50:00] You cannot scale Bob: why SOPs, playbooks, and checklists are the only scalable assets a business actually has
- [54:00] The weekly metrics review: every Monday, every week, on track or off track, and always asking why either way
- [59:00] The ten thirty-one framework: ten year vision, three year plan, one year picture, and why the numbers in the sandbox are more useful than any how
- [01:03:00] What Derek is most fired up about right now: the ten year vision he does not share publicly but references constantly
- [01:06:00] Grit defined: the tipping point, the thing that gets you through the low lows, plugging back into the why
- [01:08:00] The directive: no small children will be harmed
- [01:09:00] Dylan Bost's question from Episode 49: if you could change one thing about the world in the blink of an eye, what would it be?
- [01:11:00] Derek's answer: arrogance, and why the world would be materially better without people who use the belief that they know more than others as a weapon
- [01:12:00] Derek's question for the next guest: think of one of the darkest moments you have experienced personally or professionally, something you do not talk about much. What was the positive from it, the learning, the upside of something that has always lived on the downside?
- [01:14:00] Where to find Derek and Karl's close
Resources & Links:
- Assessment: Strengthsfinder by Gallup (focus on what you are naturally strong at and get better at it instead of trying to fix your weaknesses)
- Assessment: Kolbe (cognitive assessment on how you process information, handle risk, and approach ideation and structure)
- Challenge: The Grit Code Exposed at https://gritcodeexposed.com
Connect with Derek Fredrickson:
- Website: https://thecoosolution.com
- LinkedIn: https://www.linkedin.com/in/derekfredrickson/
- Instagram: https://www.instagram.com/derekfredrickson/
- Facebook: https://www.facebook.com/thederekfredrickson/
Connect with Karl Jacobi:
- Website: https://successwithkarl.com
- LinkedIn: https://www.linkedin.com/in/karljacobi
- Facebook: https://www.facebook.com/karl.jacobi
- Instagram: https://www.instagram.com/successwithkarl
- YouTube: https://www.youtube.com/@KarlJacobi
- TikTok: https://www.tiktok.com/@successwithkarlj
Creators and Guests
Host
Karl Jacobi
Host of The Grit Factor Podcast, Resilience & Performance Coach, Founder, Entrepreneur, Combat Veteran
