Jamie Gruber Blog/Newsletter/Becoming an Entrepreneur in Mid-Life

Thursday, November 17, 2022

Becoming an Entrepreneur in Mid-Life

This is the first edition of the 'Confessions of a Mid Life Entrepreneur' newsletter!


  • Deciding to quit my job was a ‘back of the napkin’ decision - just felt right
  • Quick math in my head was $4000 in monthly expense with $3100 passively
  • The tipping point was I BELIEVED in my ability to build my business and didn’t believe in doing the job I was doing any more
  • ​The plan was to live off limited cash flow and savings while I built my business
  • ​The actuality was other opportunities presented themselves to allow me to make $300,000 in my first year
  • ​I decided to launch this newsletter because I haven’t been transparent enough with people who are struggling in middle age to figure out how to live purposefully outside their job - and it’s time you see how messy and imperfect it is!

To get quick insights into my journey follow me on Instagram. Be sure to scroll down to see key takeaways!


I had an epiphany thanks to a conversation with a business consultant I’m hiring. I’m always asked what I do and how I make money. Lots of assumptions are made about real estate and passive income. For this newsletter, let me establish how I was paid in my W2 (which I left a year and a half ago), my plan for earning income when I decided to leave, and how I actually earn income. Then we’ll come back to the epiphany.


I was a Director of Claims for a large national insurance company. It rhymes with Schmagressive 😁. I had a salary, bonus and stock award annually and then prior stock award vesting. Here’s generally how that broke down:

Salary: $190,000
Bonus: $90,000
Prior Award Vesting: $50,000 (average)
Annual RSU Award: $50,000 (was up to $70,000)

Ironically, my salary was bumped from $175,000 to $190,000 2 months before I quit in 2021 because I had my best year of performance in 2020. When I had ‘quiet quit’, was building my side hustle and learned how to trust and delegate more to my team. A great testimonial for the concept of surrendering!

When you hear me say I left my ‘$300-$400k/year job’, that’s the breakdown.


On a long drive to Florida I started tallying up expenses. For some reason, what made sense to me as ‘base expenses’ was mortgage, car, insurances, internet connection, heat, electricity, cell phone. Those expenses added up to about $3200/month. But I rounded up to $4000 to be safe. Figured I’d have to consider health insurance at a minimum. Food and other expenses weren’t in my calculus. To me, paying for my home and the things that allow me to remain connected to the world was how I defined safety. I’m a connector - I suppose as long as I can create and cultivate connections with people that they get value from, I’m in my gift and I’ll figure it out.

So $4000/month became my baseline. That felt REALLY freeing.

Next I thought about passive income. I honestly wasn’t taking any. There was profit from my real estate but I just chose not to pay myself any of it. It just piled up in operating accounts to ensure we had our rainy day covered. My job paid me enough. But I factored in me taking distributions:

  • NY Properties: $800/month
  • Cleveland: $300/month
  • Michigan: $2000/month

That’s $3100 I could take passively (along with some syndications that paid a little to me, but I hadn’t really done many prior to leaving the job).

I’m $900 away from covering my ‘base expenses’.

The biggest consideration was Emerge and Ascend. Again, I hadn’t taken any income from it as we were/are building it. But there’s profit. Our gross profit margin was nearly 95%. Base expenses were under $5000/month and I could justify at the time taking $5000/month out of the business to pay myself a salary.

More importantly, I believed in what we were/are doing with that community. I see lives changing. I hear their stories. It made me feel alive. Full stop. I didn’t calculate an amount or a goal for income. Instead I just knew that if I’m dedicating my time and energy to helping others through this program, I’m going to be fine!

Finally, I had $120,000 in the bank earmarked as my rainy day fund (about $50,000) and to invest (about $70,000).

That was the plan. I could take passive income to cover most of my $4000 ‘base expense’, draw some income from Emerge and Ascend, cut back a bit on expenses and use the $120,000 as a burn account for a long time if I’m diligent with expenses and Emerge and Ascend does what I think it can do. Nothing written, nothing outlined, no spreadsheets. I decided in that moment that I’ll toss away that big salary and bonus based on ‘back of the napkin’, in my head math. And away I went!


I never took a salary from Emerge and Ascend when I quit. I never drew distributions from my passive investments. And I never touched the $120,000 for expenses. I did end up investing $70,000 however and keep $50-$60k as my contingency. Nothing changed.

You’re probably wondering then - how are you earning money??

If you follow my content, I talk a lot about social equity. Investing in being part of a community of like-minded individuals that you can learn and grow with. I also talk a lot about being of service to that community. My community is Gobundance. A high-net worth entrepreneurs mastermind who focus on being a ‘whole life’ millionaire. Contribution, health, adventure and relationship success is just as important as financial success in this group. For two years while in my W2, they helped me think bigger and gave me exposure to amazing people. What I learned to do was leverage my connector gift to help guys meet other guys when I heard stories that I thought would sync up well. I had no expectation of anything from anyone. It just felt good to serve. Still does!!

That drive to Florida was for my family to spend a month there. I still had my job but it was COVID, so it gave us a chance to work remotely. But before I arrived I made the decision that I was going to quit.

Word got out within my network and I got a call from Chris Ryan who is the CEO of Gobundance and a friend. At this point, I was the number one evangelist for Gobundance in the world! The community changed my life. He knew that and had a business problem that he thought I could help solve.

“Brother - we have all these people that want to join Gobundance and no good process to get on the phone with them, vet them, see if there’s mutual interest and have them join. You said you’re leaving your job - any interest in helping here?”

That sounded like fun to me! Talk to a bunch of killer entrepreneurs about something that’s changed my life? Sure. Anyone that joined for $10,000, I get $1000. For $15,000, I get $1500. So I started calling guys and had amazing conversations!! I still had my job, I’m in Florida, but I had space in my day. I talked to about 20-25 guys that month and made friendships from those 30 minute calls. For the month, it was 15 or so hours spent and when the dust settled, 17 new members joined and I got a check for $21,000!!!

A month later, we got back from Florida to Michigan and I boarded a plane immediately for a Gobundance conference in Tahoe. This was the first week of March and I had committed to myself to resign when I got back from that conference. There I met up with Mark Hentemann - someone I met by talking to him the month before and enrolling him in Gobundance. He’s the coolest guy in the world to me. $150m real estate portfolio while also being an Emmy-nominated 22 year writer for Family Guy. That’s AFTER he was a writer for David Letterman. I love his stories! He was looking to meet other people in the multifamily space as a new member and I know a lot of guys in the group. So I started connecting him, because I love doing it. We spent some time together and build a really good friendship.

“Jamie - my company Quantum Capital is growing and it’s really only me and my Chief Operations Officer. We need a marketing type presence and I’ve never seen anyone connect people and network like you. I’d love to talk about you becoming a general partner with us”

We closed on 5 apartment buildings in our first fund plus 3 more deals since then!

  • 2021 Gobundance Earnings: $200,000
  • 2021/2022 Acquisition Fees: $40,000
  • Distribution from Emerge/Ascend: $40,000 (one time)
  • ​Other affiliate income: $20,000 (i’m ballparking this)

In addition, I’ve invested in multiple syndications and see some cash flow from that and we’ve sold some of our active portfolio and realized those gains. Much of which goes into deals with Quantum so I’m invested in anything we buy.


To this day, I struggle to explain the above. There’s a lot of words there and honestly, I worry about judgment. Are you really an entrepreneur? Don’t you have a ‘job’ with Gobundance then? Aren’t you just trading time for money still? I don’t feel that way. Nothing I do is heavy. I like to work. Even if I hit the lottery, I’d still be typing this newsletter, building my brand and doing most if not all of what I do today. I love it!! This is how I define retirement. When I sit on a beach for 3 days I’m bored out of my skull. Maybe that’ll change, but right now, this is me.

My priority has been lifestyle freedom. Everything I do can be done from a cell phone. Laptop is easier for typing things like this newsletter, but I don’t have to be in one place. Hence our move to the Dominican Republic.

When I try to succinctly explain the elements of my life above, I’ll say “I have an online education company and handle membership for a high net worth mastermind group. I’m also a real estate investor with 42 doors of my own and I’m a general partner in a real estate investment company”. If someone wants the real cliff notes version, I just say ‘I’m a real estate investor’. It’s the most ‘socially acceptable’ response that doesn’t generate confusion or questions.

At the end of the day, I am the business. I’ve come to learn that I own a ‘lifestyle business’ which means the objective is to fund my life and my ability to do what I want when I want without the structure of a ‘growth business’. No level 10 meetings (so far), no profit projection sheets, no org charts. Just enough to pay the bills and live a fulfilling life.

But I’m ready for growth. I hired a business consultant who I honestly thought I was way too small for. I have a $500k year one online business and a share of the general partnership in another business but this guy works with $10m/year businesses. ‘Real’ businesses!! I opened everything to him. Cringed a bit. And he said I’m exactly who he wants to work with. Then he encapsulated EXACTLY what my business is in one sentence. Even one word.

“You help people grow their mindset and wealth through Emerge and Ascend, they become millionaires and you elevate them to Gobundance, and now they have capital to invest and they come back to you”

“You’re in the business of TRUST”

🤯 🤯 🤯

As soon as he said that, I could think of a dozen times that EXACT scenario played out. People are going to invest, but if they feel you’re genuine and authentic and your intentions are pure, why not invest with someone they know and trust?

My friend and mentor Brandon Turner does exactly that. He can raise funds in an instant because he’s been open and transparent about his life and business and seeks to serve others.


I give myself a B+ for having put out quality content for people that shows authentically what my life is about. But I want to be A+ and that starts with this newsletter. Confessions of a Mid-Life Entrepreneur is intended to give you everything that I am. The highs and lows, the takeaways and learnings, the lessons and failures - every week. I’m sure it will evolve and maybe get more succinct (although brevity has never been a skill of mine). But for now, I want to just share. If this newsletter turns you off to who I am and what I’m doing, understood. If it helps you see that the path to fulfilling work and a fulfilling life is imperfect, messy, scary but at the end of the day, doable? Even better! That’s what I hope you see.

I’m typing this from our villa in Punta Cana where we’ll be for the next year (at least). I’m excited about the future, scared about the present and fucking things up every day. What keeps me going is my family of course, and the stories I hear about others who have taken action with some inspiration from what I’ve done and what I communicate. When I lay my head down at night, that makes me smile no matter what fears or concerns I have.


#1: Vulnerability is hard but necessary!

When I spoke to that business consultant and shared everything, I felt like a damn mess. But I also felt lighter. Whenever I share my OneSheet with my accountability group in Gobundance I clench. But it always feels like a weight is lifted after. Sharing what I have in this newsletter was a complete mind-fuck. I delayed forever out of fear of judgment. But you can see how much flowed out of me!! Getting around people that will support you instead of judging you and then sharing honestly is the path to growth. I know it and so do you.

#2: Prepare…but at some point you have to jump

I don’t have the engineer or analyst brain. I go on gut feel and mental math. Even with the biggest decisions in my life. I think pro/con lists are bullshit. I can have 100 pros and 1 con - but if the con is ‘i’ll die’ then I’m not doing it! To quit my job, I had savings, a business that wasn’t paying me anything and an amazing network. I talk to so many that say ‘once I’m at $10,000 a month” or “after my kids are out of college”. For the majority of people, those are just excuses. And boy do people dig their heels in on why it’s not. They have their logic and reasons why they CAN’T. But they’re excuses. Period. And if you want to fight for your excuses, you get to keep them! As an aside, if our 7 or 4 year old stub their toe and say ‘FUCK’ I have no issue with it. We’ve told them that. But when they say CAN’T…they’re getting an earful from Dad!

#3: The target you set to exit comes faster when you exit

A friend has an objective to get to $40,000 a month in passive income before quitting. He’s at $25,000/month now but feels that’s not enough. Hey, it’s his journey but he’s as crazy as those last two sentences indicate he is. His timeline is nearly a year from now. What I try like hell to explain to him, because I’ve seen it countless times with others, and even illustrated this with my story above. He’ll hit that $40,000/month WAY faster than a year from now if he quit today. You get aligned. You get focused. You get moving. I don’t advocate just busting the doors open and quitting without anything to run toward. Build the thing. Buy the business. Invest in the asset. Whatever it is, have something to run toward. But whatever the goal is for you to leave your job will happen faster when you leave your job. A rule of thumb for me is when you hit 50-75% of your expenses and see growth in whatever you do, and have 6 months in the bank - you can quit. ‘Should’ is personal choice. But you can!


Tribe of Millionaires Podcast Episode
✯ Check out episode 227 with Keala Kanae. He talks about starting and scaling a business. I loved everything about his message. Something Funny I Saw Mark Normand on Instagram is hilarious to me. He does these call outs to the audience to give him a topic - like a juke box - and then gives his take. Check him out!

This Annoys Me
✯ Pizza has certain principles to be pizza. It must come from a place that ends in a vowel, it must fold, flop and drip grease down the middle, and lastly it must have something that people from the midwest don’t have in their pizza. It’s a key ingredient that seems to be lacking in any pizza outside of the northeast extended to MAYBE Baltimore. That ingredient .. is taste! The cardboard squares with ketchup on it that places like Jets or other wannabe ‘pizza’ places provides meet NONE of the criteria above. And anyone that thinks that meat pie called ‘Chicago style’ is pizza can simply unsubscribe. I feel better.

Lesson from Living Abroad
✯ I saw 4 dudes in a car with their hands holding a stack of plywood to the roof - nothing else tying it down. They lack resources here but are incredibly resourceful. Makes me realize how resource rich we are in the US and Canada which can diminish our ability to be resourceful. Combining the two makes you unstoppable!!

If you’d like to work with me and/or be part of my communities
Join Emerge for our next launch you can get it for only $1495 (use code JAMIE for $500 off!!)
✯ If you’re a net worth millionaire, apply here to join Gobundance and my team will schedule a time for us to talk. It’s $10,000-$15,000 annually to be a member - the greatest investment you can make in your future!

Talk to you next week
- Jamie

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