"How I Did It" Series with XYPN Member Dillon Cobb

7 min read
February 12, 2024

We're excited to share another member story from our "How I Did It" series.  

Deciding to take the leap to start your own financial planning firm can be very scary. And actually "leaping" can feel overwhelming. There are so many decisions and responsibilities. How am I going to make this work? What business model should I use? How do I manage compliance? How do I market myself? What's this going to cost?

While the questions are the same for advisors starting their own RIA, their decisions are as individual as the advisors making them. In this peer-to-peer guest series, we take a deep dive into those decisions as XYPN members share their stories, resources, regrets, and successes experienced while launching their financial planning practice. 

Looking for a roadmap to start your own independent RIA? Check out our  comprehensive guide to starting your firm!

Today's guest author, Dillon Cobb, CFP®, CPA, shares how he launched his RIA, Simply Human Advisors. He recounts his journey—from the death of his best friend who became his "Why" to the "life support" of his XYPN mastermind groupand details the resources and first-year expenses it took.

Dillon Cobb Blog #1

From left to right: Bradley Hilton, Dillon Cobb, Andrew Gray, Dillon Kenniston, and Allen Mueller

How did I do this? With personal and professional mistakes and a whole lot of grief thrown in.

I spent too much money, tested every technology under the sun, and tried to be perfect before anything was complete. My first hired contractor was a local web developer, and six months later, I fired them with nothing to show for it. Personally, my wife started a new job, we moved houses, replaced two cars, and enrolled our kids in private school. Skip ahead to the end to find out which ones were mistakes.


Let's start with the big picture. I am a CPA, raised by a CPA. This line of work is in my blood. With experience in audit, banking, tax, trust, estate, and financial planning, I had the background but also an acute awareness of the risks of failure and the headaches of being the boss. I was a steadfast soldier/supporting actor, never the general/lead actor. Like anyone else, I would get frustrated by leaders, bureaucracy, technology, processes, and more, but I knew my lane and stayed in it for over 15 years. That is until my best friend was killed in a car accident in March of 2021, the day my world flipped upside down. I did a brief video about our friendship if you have 3 minutes. His death was a tectonic, life-altering shift. 

Dillon Cobb Blog #2


Until you have had something deeply shatter your life, it is hard to describe how different you are on the other side of tragedy. Every single truth I held onto was on the table for further examination. Going back to my old firm was no longer an attractive option. I still struggle with anger and sadness. However, time became my most precious gift, and I wanted more control over mine. At the same time, my calling crystallized: a growing desire to help people who have experienced their own tragedy. Today, all of my clients except one have experienced a divorce or death, and a few have experienced both. 


Starting my own business was not the plan, and we had no significant assets set aside. We were not prepared for this. On the other hand, I could count on my wife's job with good pay and excellent benefits. We could get by, barely, with her salary for a short period until I could get up and running profitably. So we jumped. In January of 2022, we started making plans, and my last day on the job was in May. By July 2022, Simply Human Advisors was approved for business in Texas. 


The immediate hurdle was my non-accept/non-solicit/non-compete within 35 miles of my previous office for one year, which was limited enough to be enforceable in court. Beyond the legality, my previous employer and I wanted to maintain a good relationship. I was different than when they hired me. I knew it, and they could see it. We parted amicably, but I could not take clients with me, which meant I was building from scratch. 


Michael Kitces and I met at a Schwab education session ten years ago, and I have followed him ever since. XYPN was on my radar from the beginning, and it was a no-brainer when I made the jump. I subscribed to XYPN a few months before I left my old firm and roughly four months before Simply Human Advisors was approved.

My mastermind group of Allen Mueller, Andrew Gray, Bradley Hilton, and Dillon Kenniston are instrumental in my success. Our unique bond formed as we walked side-by-side down a similar path, and continues growing into a group of great friends and trusted advisors. XYPN formed our "Maroon Mallards" group, and by the sheer luck of the draw (or maybe XYPN's master plan), we have become invaluable to each other. We continue sharing technical tips, but the value goes much deeper than the technical expertise. We meet weekly via Zoom, have a shared Slack channel, and coordinate meeting in person at one or two conferences each year.

Before XYPN LIVE 2023, I went to Atlanta early and stayed with Bradley's family for a few nights. Our group makes a point of stopping and celebrating wins as they come. We devote time during the week when one of us has a health, marriage, or business struggle to love and support one another. These four guys have supported me as I continue to grieve the loss of my friend. I cannot emphasize how crucial having this support group has been to my success.  If you'd like to hear more about our group, check out our XYPN Radio podcast episode with Andrew, Allen, and me. 

Not to sound trite, but XYPN made this happen, and it goes much deeper than pairing four random strangers together. (Side Note: Andrew introduced Bradley to the group at XYPN LIVE 2022, and we added him to Slack and Zoom the following week.) Beyond the introductions, XYPN fosters an environment of abundance, support, acceptance, kindness, excellence, growth, perseverance, and much more. The level of encouragement from random people you meet, who would ordinarily be "competition," is extremely rare. Add in the atmosphere of an XYPN LIVE conference, unlike any I have experienced in more than 15 years, is a culture that builds success stories when failure would be more likely by yourself.


Because of my years of experience, I knew I needed my processes to be different from what I had known. Optimizing for the most money, or even efficiency with money, was no longer my personal goal. I realized the people I wanted to work for would also not identify "most money" as their top priority. After much research, MoneyQuotient rose to the top as their approach focuses on the process. I began their coaching program before my firm was approved and built my onboarding process around their framework. Words are not enough to express how profoundly this has shaped my onboarding. Clients are communicating with me in ways they never would have before. We are getting a deeper and more focused "why" and building finances around that. 


Although my mastermind support, my processes, and my newfound purpose have been crucial, I could not do this without the complete support and encouragement of my wife, Talan. If at any point she wavered, I might have failed. Together, we recognize that under different circumstances, certain big decisions might have been different (for example, moving and buying an RV.) Talan and I are two headstrong people going through a difficult transition with many changes. Often, this can lead to a disaster. We have experienced significant sadness and grief and often unloaded stress on each other, but we have never doubted our commitment. Talan is the strongest person I know, and her unrelenting perseverance and tenacity are a huge part of my being able to build this business. There have been moments when I was ready to turn back, and she would not let me. She encouraged me to keep fighting. Again, having her support throughout this process has given me strength. 

Dillon Cobb Blog #3


Below are the expenses for what I spent on my business to start:

Simply Human Advisors Expenses


"There are no mistakes, only lessons."
― various notable people


"The solution to an overbusy life is not more time. It’s to slow down and simplify our lives around what really matters.”
John Mark Comer, The Ruthless Elimination of Hurry 

“Our faith is not a facade we erect to convince ourselves and others that pain doesn't hurt―it is an oak tree that can withstand the storms of doubt and pain in our lives and grow stronger through them."
Vaneetha Rendall Risner, The Scars That Have Shaped Me

“Don't aim at success. The more you aim at it and make it a target, the more you are going to miss it. For success, like happiness, cannot be pursued; it must ensue..."
Viktor E. Frankl, Man’s Search for Meaning

Your firm, your terms. It can be done. Show me how.

Dillon Cobb

Dillon Cobb

CPA and CFP by training, Servant by inclination. Serving people who are hurting has always been my natural instinct, and God-given gift. However, it was during my period of intense grief that my calling crystalized. Simply Human Advisors was built to serve those who are grieving.

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