[USER]

My best friend just inherited a good amount of money (a few hundred million dollars) and he asked me to start a business with him.

The business goal is to help people that come back from the military to become private contractors. We have very different backgrounds.

He has been in the military since we left high school, I became a sillicon valley engineer and hop around tech companies.

The reason why he asked me is I have been working at some big companies like Tesla, Amazon.

Part of me wants to take this opportunity to do something big and cool, but I am a little nervous because I have never run a business before.

Would you take this opportunity if you’re in my shoes?

[Scott]

Sounds like a great way to turn a few hundred million dollars into a few million dollars.

[Kitty]

Woah. Why is he asking you if you have no background? Does he have any business plan or concept at all? I would be vary wary here.

If you want to somehow steal his money I guess go into it, he doesn’t have a good handle, otherwise tread lightly (my last point was a jokeeee)

[Daniel]

I think it’s a solid idea. If you end up pursuing it, please do reach out. I’m working with some folks right now on figuring out how to help veterans transition back to civilian life.

We are focusing more on the affordable housing angle, but jobs are a big part of it.

As far as your question goes, before starting a business with anyone, I would definitely spend more time to understand each other in terms of your expectations for each other and how you would plan to resolve conflicts.

In addition, having a clear, shared vision is important so you all know what you are working towards. A clearly defined operating agreement is critical.

In regards to financing, I would recommend trying to bootstrap as much as you can.

It’s nice to have a partner with resources, but unless your intention is to be his employee rather than partner, I would focus on building out the proof of concept with as little resources as possible before really taking it further with more capital.

[Molly]

The first thing any sort of Partnership needs to figure out is the “divorce” terms. You can get Free Mentors from SCORE, an SBA Affiliate.

Their website has Lots of information.

Sounds like something worthwhile. Will it be For Profit, or Non Profit organization?

[Robert]

By your own admission, you’ve never run a business before…. The best thing you can do for the individual; especially since you have said he is your best friend is to say the following (or a variation thereof) “ since you are my best friend; and since I don’t like mixing business and friends; and since I also have no experience whatsoever running a business, the best thing I can do for you as your friend is to tell you to find a person or a number of people who have in fact, run businesses; and:or started up businesses, and go from there.”

you probably also would be doing your friend a huge favor if you told him the following ——-> “ I realize you have inherited a huge amount of money; but statistics show that 50% of all people who get a windfall – lottery winning, inheritance, large, personal injury settlement……

Five years later 50% of them are flat broke. Since you are my best friend, I do not want you to become a statistic.

PLEASE wait at least six months before you do anything with this money.”

[Sara]

Why would someone who just inherited hundreds of millions want to start a business that he needs help with?

Plus, that business concept sounds like it should be a charity.

[Jenn]

If he invests that money in index funds, he’ll make more of a profit without having to do any work.

If his goal is to help people and it’s not about the money, that’s another story, but both of your goals should align if you’re going to team up with him.

[David]

Could it work? Sure… but it sounds like a recipe for getting in over your heads and damaging a friendship while draining a fortune down.

I wouldn’t mix friendship and business when neither of us had run a business before unless it was the sort of side hustle that didn’t really matter if it worked or not.

But the type of person who takes the big risks for the possibility of doing something big also doesn’t listen to what strangers on the internet say. So, you do you. But I wouldn’t.

If I was going to try something like that, I’d want to start with small ambitions. If y’all come out with huge plans early on, it’s liable to be more than you can handle.

Also, when someone suddenly comes into money, don’t make big decisions for a long time. Your brain can’t really grasp it for a while.

Also, he has a new fortune to fall back on. If this blows up, are you set up to be fine financially giving up what you do now? Even businesses that succeed, don’t make money at first.

[Boris]

He could put that money in the market and use dividends to help the veterans unless he wants a hobby/job/thrill or a business.

[Ami]

Based on personal experience experience, I will never work with family again and would extend that caution to working with friends as well….

unless you don’t want to be friends any longer.

[Irfan]

Since you are coming from Tech, most of the tech founders usually don’t have background in running or building companies, I would treat it as a start up, do the dur diligence, Product market fit, competitors, persons and what pain point you will target.

Job placement market place for vets is attractive and have funding opps as well.

Dont worry about naysayerss, use this opportunity to build something valuable in this space.

[Quang]

Wow, this sounds like an incredible opportunity, but I get why you’re feeling nervous—it’s a huge step. If I were you, here’s what I’d think about:

First, sit down with your friend and really hash out the vision for this business.

What’s the big picture? What does success look like for both of you? Are you both equally passionate about helping veterans transition to private contracting?

It’s super important to make sure you’re on the same page before jumping in.

Next, think about how your skills fit into the business. You’ve got this amazing tech background and experience working at companies like Tesla and Amazon—that’s huge.

And your friend’s military expertise complements that perfectly. But you’ll want to define clear roles early on. Are you focusing on tech, strategy, or operations?

Figure out who’s responsible for what so you don’t step on each other’s toes.

Also, since you’ve never run a business before, it might be worth brushing up on the basics of entrepreneurship.

There are tons of resources out there—books like The Lean Startup or Zero to One are great. And maybe even find a mentor or advisor who’s done something similar and can guide you.

One big thing to keep in mind: mixing business with friendship can be tricky. You’ll need to protect your relationship.

I’d recommend drafting a partnership agreement that lays out things like equity, decision-making, and what happens if one of you wants to step away.

If you’re still unsure, maybe start small. Run a pilot program or test the idea with a small group of veterans to see if it works. That way, you’re not diving in headfirst without knowing if it has potential.

And let’s be real—your friend’s inheritance gives you a cushion, but this is still a risk.

Set a realistic budget and make sure you both know how much you’re willing to invest before you start.

If it were me, I’d probably go for it—but only if I was truly excited about the mission and saw a clear role for myself. A business like this could be a game-changer, but it’s a lot of work.

Taking a 6-12 month trial period to see how it feels might not be a bad idea either.

At the end of the day, trust your gut. If this feels like a once-in-a-lifetime opportunity to do something meaningful, it might be worth stepping out of your comfort zone.

But make sure to plan carefully and communicate openly with your friend. You’ve got this!

[Ellen]

Sounds like his “business” venture is more of a charity foundation. Helping veterans find jobs is a fantastic thing to do, but I would not go into it with the mindset of making a business out of it.

Business is about turning a profit. Sounds like your friend wants to use this money to help veterans, not profit off their situation.

By all means he should do it, but he needs to educate himself about the best way to achieve his goal, not ask his best friend to risk their friendship to enter into a business that neither know anything about.

[David]

You’ve got a career and with a few hundred million dollars, your buddy is looking for a hobby.

At best, a for-profit (you didn’t say it was a charitable organization) company targeting veterans wanting to become private contractors seems like a late-night cringy informercial.

Unless you mean Private Military Contractors (PMCs) like Wagner Group or Academi – what Blackwater eventually became.

Now that is a growth industry and will get even bigger in the coming years. If he wants to start a PMC, definitely get involved.

Otherwise, keep growing your own career until he gets his idea off the ground.

[Michael]

I have a similar background as you. I make great money and have tons of free time. TBH not sure I would risk that to start a business with no experience.

Especially in the field of military vets which is often problematic.

Good luck whatever you decide to do.

[Kate]

This is your chance to do something very meaningful with your life and give back while also having a safety net of best friend backing it up financially.

I’d do it in a heartbeat.

[JB]

Do you have the skill set to do the computer programming needed for the company?

If yes, tell him you can do a back office type of work with him, but you’ll need either 3rd partner or to hire someone with the skill sets and contacts to work in private security.

You’re literally entering an arena of killers and extremely dangerous types of people and will have clientele that could be doing less than legal things so you’ll need to see if you have the mindset to deal with that.

[Georgie]

With that kind of money… Surely you would be able to fill the skills shortages with very competent people with proven track records…

[Susie]

Running a business and being a W2 employee are completely different mindsets. Do you have the desire to run a business?

Do you actually want to learn how?

It sounds more like a charity than a business and although a charity can make you money through whatever your wage/perks are, it isn’t quite the same IMO.

In my business, I’m never really off work. But I’m off a lot in my W2 job….

[Jessica]

This concept exists already, so many times over. It’s mostly done by non-profits.

I don’t see how helping vets land contract positions could be a profitable venture.

I wouldn’t waste my time if I were you.

[Author]

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