When to Go All In On the Side Hustle

I work at a $200mm AUM family office in TX as an investment analyst. I’m compensated fairly at low 6 figures.

My job is great overall. I have a good WLB and get hands-on exposure to deals and portfolio company support. Was told I am doing great and will be promoted middle of this year. My only real complaint is that I spend probably 85% of my time supporting one portfolio company that I don’t find overly interesting. It’s an underperforming deal with a lean back office, so I’m heavily utilized to perform analytical duties and help with reporting. I joined the firm to work on new deals, and I’m not thrilled with how much of my time is spent doing repetitive, mundane tasks for this one company.

Anyways, because my WLB is solid I started a side hustle last year which has taken off. YTD I’ve earned over $60 grand and spend on average 10-12 hours per week on the side hustle. It’s easy and not time intensive.

Would I be dumb to jump ship soon-ish and just do the side hustle full time while I explore other avenues of income and business models? I’m pretty entrepreneurial and a good chunk of my waking hours are spent brainstorming how to make money in fun/interesting ways. All of the repetitive excel work is really taking a toll on me and it isn’t my natural inclination to find enjoyment from these tasks.

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Transitioning from side hustle to full time requires entrepreneurship. You demonstrate some of that as this occupies your mind. That's actually step one and critical for any chance of success. For those that say you need to wait until you reach x or 2x income, they are missing the necessary risk taking attributes of a successful entrepreneur. They are looking for security. Starting/running your own business is about opportunity. Your skillset and confidence are your security and then you make it happen.

I've run my own organization for over 25 yrs. Was doing well as an employee (in sales) and figured I could do way better on my own (expand my product line, territory, relationships, service offerings, etc.) Life immediately goes from security to 100% production / revenue creation. My friends used to say things like, "Wow I could never do something like that" or "How can you put in all that effort not knowing if you'll get paid?" I would internally think, "How can you put in that effort knowing that's ALL you'll get paid?" Just a different mindset. Fast forward after building a solid business, my same friends think I have it easy, don't really have to work hard, don't have to deal with the complexities of corporate America, etc. I built my future. Wasn't easy but I had that mindset.

If you're that guy, you'll know it. Most people you run in to on this site are not the right mindset to ask. They aren't risk takers AT ALL. They are the opposite. Good school > good job > promotion track or MBA > better job, etc. That's great and I wish them well. They can do fabulously well. Most won't but they will be OK. The ones that break out to do their own thing will fail at a very high rate, BUT most of that is because they weren't the right rock. Have a friend who left corp sales (VP level) to build a solar company yrs ago (probably too early). He frequently asked my opinion / wanted guidance. He never really left employee mindset. He was looking for an investor (found one) and was totally focused on a two yr guarantee of $x. Secured it and basically had the underlying attitude of "if this doesn't work I'm still getting paid for two yrs and then I'll figure something out." Unless pure luck is involved in a major way, can't have that attitude. Have to be able to gut it out. Unless your side hustle is day trading, most start ups are about sales. You have to be able to sell. You have to get checks or your idea is just that, an idea. If you have a good idea and can sell it, you're on your way. Now it's about building an organization around you for growth. But it's first and foremost about sales! 

Are you that guy? Nobody but you knows the answer!

 

Highly recommend reading "The E Myth: Why Most Small Businesses Fail and What You Can Do About It" by Gerber. Quick read, fantastic story format. Clearly lays out the challenges and helps you identify who you are:

1. Employee

2. Manager

3. Entrepreneur

Shows how most businesses fail because all the employee / owner has accomplished is creating a job for themselves, not a business that can operate without them. Takes you through the journey of a solo operator and walks through the steps necessary to becoming an actual sustainable business, not just a corp or LLC by registration.

I've read it many times and it rings true for different reasons each time. An attorney friend of mine suggested it over 25 yrs ago. He successfully transformed his practice into a business with many other attorney's as his clients. As the book constatnly repeats, he learned to "operate on his business, not in his business". That's the secret.

Nothing wrong with hanging a shingle and being your own boss, but essentially you're still an employee with far fewer resources.

Sounds like your side hustle is in a different arena all together (than your job), so all the more reason to read the book. If you're an entrepreneur, you'll enjoy it.

 

Be risk averse and open to working very long hours. Have a few in my extended family and two of them are multimillionaires. One of them sold his company in the 90s for somewhere between $20-40M and at one point was working 8am - 3am nights consistently. Other one is in his 40s right now and is amazing at selling but there are some years where he was on the road internationally for ~3-4 months annually (has a spouse and a few kids).

 

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