👋 Hello! Why are we here? Why are we talking about feet pics?

We’re talking side hustles. Or, as I’ve expertly rebranded them, “side bets.”

W2 work is nice. You get a paycheck. You get health insurance. You get a lot of Zoom meetings.

But, there’s more. I’ve always been jealous of people that have figured out the unknown realm: the self-employed cash cow. I’m jealous of the folks that can work for fewer hours and see outsized returns. I’m jealous of the 11 AM golfers, the midday massage-getters, the “hey let’s go get Mexican food in Santa Barbara right now” crew.

It’s not for riches. No - it’s for peace of mind, in case you ever face the agonizing feeling of losing your stable job. It’s for additional revenue, to pay for a newer car, or a backyard refurbishing, or an unexpected HVAC repair. Peace of mind is priceless, and that’s why I started this adventure.

I’d also like to buy a nice watch. Sue me.

I’m going to explore side hustles. I’ll figure out which ones work, and which ones are silly. And I want to document the good, bad, and ugly for everyone else as I work through it. And, as the subject line indicates, I’d prefer not to sell pictures of my feet for money, so we’ll avoid the “sindustries.” As much as we can.

…no promises tho.

There are countless LinkedIn / TikTok / IG influencers touting the ease and the efficiency of side hustles, and why everyone with a W2 job is a sucker. From what I can tell, most of their advice is murky and often requires a bunch of money upfront to start (real estate, for example). They seem to want you to buy their stuff, fail, and buy more. (Justin Welsh is an exception, I like his stuff).

I’m aiming to be the antidote to all that noise. A real person, relatively well-positioned in his career, but looking for more, and willing to fail a bunch and share all of it with y’all.

💵 How do I decide where to place my bet?

My biggest problem with all of this, always, has been: how the heck am I going to decide where to dedicate my time, and give myself the best possible chance of success?

A lot of the side hustle influencers say to buy a small business or invest in a franchise or use your existing pile of money for X, Y, or Z: cool, where is the $20-100k upfront investment coming from? I don’t have family money, and every additional penny in my bank account goes to my kids or property taxes or fixing bad laminate flooring.

So - how can I do this without spending any initial capital?

Limited money is one consideration, but there’s more; here is the full list of requirements:

• Limited (or no) capital requirement

• Limited time commitment - I have a full-time job that requires my attention in business hours (and sometimes more than business hours). I have to be able to do this with 2 hrs / day max

• Passive - so I can build something to sell, then sit back as people order / consume it. Aim to ‘make money while I sleep’

• Passion - I want to care about what I’m spending time on

• (No feet pics)

🤔 What can I offer right now?

What do I have - knowledge, skills, etc. - that I can use to start a side bet? (You should ask yourself the same question, then document some options.)

I have:

• An advanced degree from The University of Chicago

  • Cool, that means I have a better chance of landing a normal job because I paid a lot of money for a piece of paper

💬 btw...MBA degrees are getting a lot of heat lately - lots of discussions about the actual ROI of the expensive degree. FWIW, I didn't learn a ton of practical skills during the course of my MBA studies - I learned mostly about bars in Chicago and wearing suits on planes. However! Going to graduate school is the only reason I was able to transition from finance to marketing / sales. In my opinion, based on the work I like to engage with, it was well worth it. 

• An in-depth understanding of the cannabis industry, related technologies, and alternative medicines

  • This is helpful, but how can I leverage this knowledge to offer something of value to my potential customers?

    • OPTION 1: Consulting - I could hang a shingle and land part-time, contract-based projects

    • OPTION 2: Building a business around alternative medicine products. Cannabis, mushrooms, etc. Products, retail, etc.

• An in-depth understanding of selling saas for an early-stage startup

  • Same as OPTION 1: Consulting

• A following on LinkedIn that I’ve built over seven years

  • I have about 27k followers on LinkedIn that seem to like what I have to say about cannabis, parenting, startup sales, life in general

    • OPTION 3: Leverage audience to sell them something

📝 Option Review

That exercise took me five minutes, and I have three options to consider for my Side Bet. Let’s review

OPTION 1: Consulting for cannabis companies and/or alternative medicine companies; consulting for sales orgs

OPTION 2: Building a business around alternative medicines. Cannabis, mushrooms, other alt meds

This one is interesting, because the answers to my requirements depend heavily on what I’m selling and how I go to market.

For example: opening a cannabis retail shop requires a lot of capital, a lot of time, and is decidedly not passive.

But! Setting up a funnel for mushroom supplements or hemp beverages or other useful products and entering into a drop-shipping arrangement with a manufacturer is relatively cheap, takes much less time, and is somewhat passive.

💬 btw...drop-shipping is interesting to me. Here's the definition: 

"to move (goods) from the manufacturer directly to the retailer without going through the usual distribution channels."

Meaning - you don't buy or hold inventory. When a customer places an order with you, a manufacturer labels and ships products directly to the customer, then charges you some margin. 

If executed well, it skips a lot of steps in the supply chain, and you can focus on marketing and sales (instead of manufacturing and distributing). 

OPTION 3: Leverage LI audience to sell them something

I haven’t asked much of my following over the course of many years. It stands to reason that some people would buy stuff from me. The question is: what would I sell? I’d have to build a business in the background to have something to sell.

But - what if it’s not a physical product? What if I take a step back and get a little meta? I’ve built an audience that has been extraordinarily useful in my career - we’ve closed deals at Jane because people feel like they know me, or they respect what I have to say. I’ve also been gifted opportunities for being recognizable in the industry - speaking events, panels, that kind of thing.

So - what if I teach people how to build an audience like I did? So they can enjoy the spoils of their content like I have?

That tickles me the right way.

The Verdict for the First Side Bet

Given my review of my options, I’m going to aim at creating and selling an online course, teaching others how to build their niche audience on LinkedIn, like I did.

(Btw, I’m going to make decisions quickly like this and embrace failing fast. 10% planning, 90% execution and testing).

Next Steps / How This Will Work

It took me ten minutes to select this option - next step is to get into deep research on how to actually do it. I’ll share my steps, my failures, my successes, everything.

Stay tuned. If the journey is interesting to you, please share this newsletter and talk about it often.

And subscribe. Right down below. Right now.

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