How much is enough?

Which outcome would you rather have? Please humor me and help me to figure out what really makes sense for me.

1. Stable job in a LCOL city, running the family business and taking 1M personal income. You have control of your schedule, golf when you want, and spend as much time as you want with your family.

2. You are in the PE world in a LCOL city, trying to build a roll-up vehicle in a specific niche. You are taking 250-500k personal earnings but have a chance at a 50M outcome if the platform scales and exits. Your lifestyle is hectic, you have less free time, but you are building something that is yours. While you are taking significant risk, you have a shot at lottery ticket upside.

3. You go the NYC PE route, you manage to make partner and are pulling 4-5M cash a year with massive carry checks coming in (let's assume it actually pays out). You are absolutely grinding and rarely have time for your family or kids.

27 Comments
 

Just wanted to get perspectives from people that are older to see if what I am striving for is worth it or if I should work in my family business.

 

The fact that Option 1 is actually something you have access to and you’re considering NOT doing it in favor of some bullshit hardo fantasy is a slap to the face of all us morons that got into this field because they came from nothing and needed to make money. Jesus Christ I hate this forum.

 

Are you presenting options you actually have available to you? If so, Option 1 is a no brainer unless you're incredibly ambitious in the business world and have no other interests outside of work. I think for most people Option 1 would be a salary significantly lower, so weighing these choices is more difficult due to more trade offs.

just read it
 

Yes these options are available to me. Really trying to weigh options 1 and 2 moreso. I like the idea of building a rollup but feel like I am underestimating the difficulty. I am also not overly ambitious.

Really just wanted to get people’s thoughts on what truly is enough because I have kind of been desensitized due to being around highly successful people in college and growing up.

 

Intern in PE - LBOs

Yes these options are available to me. Really trying to weigh options 1 and 2 moreso. I like the idea of building a rollup but feel like I am underestimating the difficulty. I am also not overly ambitious.

Really just wanted to get people’s thoughts on what truly is enough because I have kind of been desensitized due to being around highly successful people in college and growing up.

Is the family business something you're interested in taking over?

just read it
 

Option 1 is the true ideal IMO. But for some of us sick fucks "enough" isn't a term we're very comfortable with. There's always some black swan event hanging out in the back of your mind that makes you want more so you can feel confident facing any situation no matter how unlikely it may be. 

"If you don't have any enemies in life you have never stood up for anything" - Winston Churchill | "It's a testament to the sheer belligerence of the profession that people would rather argue about the 'risk-adjusted returns' of using inferior tooth cleaning methods." - kellycriterion
 

I've done all three:

  1. My family business was in a HCOL. Constantly fought with my dad. I was just a highly paid employee. Our company's employees thought I was just an inherited idiot. If you're driven/smart/motivated you'll want to do more than just be a freeloader. I wanted to do things differently but dad had the final say. He was more conservative given his age and I wanted to continue to reinvest and grow the business. Got frustrated, ended up treating it like a corporate job and ended up partying, going out, w/e working 40 hours a week for a couple years. Felt unfulfilled and wasn't hitting my true potential. Always felt that would be overshadowed by my dad. 1 mill a year isn't that much honestly too in a HCOL.... and living in a LCOL sucks. It was great experience though for actually learning how to run a company before my next project. 
  2. I ended up going this route after leaving my fam businesss. For the sake of my relationship with my folks, this was the best route... so I left the family business. My parents helped fund my downpayment along with with my own personal savings.  Did a larger deal though outside of SBA size. Rolls up are tricky to execute and infinitely more stress. One bad deal can bankrupt you. Had a ton of growth my first couple of years. Industry tailwinds have cut my EBITDA by 25-30 percent since my peak, before debt payments. Employee bullshit, competitors trying to screw you, etc. I don't think anyone realizes how tough entrepreneurship is. Looking back, I wouldn't have done it again and PG'd millions of dollars of debt. I don't think there is really anything like a "lifestyle business" (and if its being treated like one, a competitor will eat you alive). 
  3. I did the banking + PE path before fam biz/ETA. I worked more aggregate hours. Always thought to myself, why am I working so many hours if I can work for myself? Well guess what, in entrepreneurship you're working as many hours with way more stress and risk. At my age I'd be making a comfortable 1-2 million a year in finance if i stayed down the path. Sure my net worth would be less than it is now, but I would have had a much smoother life.... maybe been married now and had kids. 

So if I had to do it all over again? I would take option 3, but be a partner in LMM PE or start an SBIC down the line. I love investing and growing small business, but hate operating. 

If you're more technical would suggest going down the AI Route. Infinite money to be made with the right VC play. Have classmates from my Ivy who are worth couple hundred million/billion on paper. This was the highest risk/highest ROI path. 

 

When you say the AI route, what do you mean exactly?

I am much more social then technical, but want to find a path where I can lean into this.

 

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