"When I Grow Up, I Want to Be A Sales Player!"

Wait! Before we get into the topic of today’s newsletter, I had to share this…

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My son brought this home from school the other day and I just about died laughing 😆

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(Yes, here in Phoenix, AZ, kids start school in July, which makes sense, since they get longer breaks in the Fall, Winter, and Spring when it’s not 110 degrees out. But I digress.)

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For most of his life, he’s known his dad to be a Sales Player, but I never imagined he’d skip right over astronaut, firefighter, or pilot… and choose sales as his dream job.

And the illustration? Nailed it.

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So, this week, when you’re on cold call #55 of 80 and ready to bang your head on your desk, just remember, somewhere out there, there’s a kid who thinks what you do is super cool.😂

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Alright, now let’s get into it…

Re: Side Hustles...

Let’s talk about something that comes up all the time in my DMs and conversations with SP community:

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“Should I start a side hustle if I’m working in tech sales?”

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It’s a fair question, especially in a market where job security can feel shaky 👀

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Maybe you’re crushing it. Maybe not. Either way, the idea of building something outside your 9-5 is hard to ignore.

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But here’s the truth:

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👉 It depends.

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If you’re in a high-upside AE role (closing six-figure deals, earning strong commissions, and climbing the career ladder) your best “side hustle” might just be closing more deals.

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But if you’re not there yet (or feel stuck), a side hustle can be a smart hedge, as long as it doesn’t become a distraction.

Here are a few side hustle ideas that can actually work well for Sales Players who are looking to create multiple income streams and scratch their entrepreneurial itch:

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1. Freelance biz dev: For a while, I was helping a recruiter friend source new clients and searches. I’d send a few cold emails at night, make intros, and get a cut when she landed a contract. Low effort, real income. Every B2B company needs these services and as a Sales Player, you are uniquely qualified to help with your skillset.

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2. Niche lead generation and web design services: I used to run Facebook ads for dermatologists (long story) But it made $1-2K/month before I shut it down (managing clients became too overwhelming, while also trying to hit quota and starting a family). I also spent a year or so helping multiple companies rebuild their eCommerce websites. For this I even hired a developer, who was based in Mexico to help with the technical stuff. Service businesses like this can be easy to start and scale if you’ve got a clear niche, but finding the right clients and delivering results can be tough to sustain if you are still selling full-time.

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3. B2B affiliate marketing: Most SaaS/AI tools have partner programs. If you’re already recommending products to your network, why not earn commission? Start with tools like PartnerStack or just reach out directly to your favorite vendors. I've worked with some great companies (like Surfe - *yep, that's an affiliate link) to get paid for recommending tools I already use.

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4. Consulting or done-for-you services: Got a superpower? Sales ops, outbound strategy, CRM setups, writing good email copy, package it up and sell it! Outsource the fulfillment if needed and focus on what you’re best at: selling and managing client relationships.

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5. Content creation: The podcast started as a creative project, and now it brings in a steady income. It’s by no means “fast money,” but it is a long-term asset if you stay consistent and grow an audience over time. Having an audience or a following will open up new networks, relationships and opportunities to sell your ideas in the form of coaching (my main revenue stream), consulting, courses, books, sponsorships or even brand deals (if that's your thing). The best way to start is to start sharing your own learnings and journey. I know, I know, creating content is super saturated, I once heard someone say it is the world's most competitive marketplace, but what do you really have to lose?

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Before you launch, a few important considerations:

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Check your employment agreement. You don’t want to end up in a meeting with HR. Be smart. Avoid conflicts of interest, especially if your company sells to the same audience.

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Protect your energy. If you’re in a high-earning role, ask yourself: would this side hustle be additive, or a distraction from making bigger commissions?

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Think about the long game. A good side hustle builds skills, relationships, and future freedom, not just extra cash.

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If you’re thinking through a side project and want to bounce around ideas, reply to this email or DM me on LinkedIn.

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See you next Sunday,

-Jesse

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P.S. Want to hear more about this? I broke it all down in this podcast episode (link to episode). Worth a listen if you’re in brainstorming mode.