How I made my first $5k online

Turning nothing into something. Something into money in my pocket.

May 25, 2024

In case you’re new here, I host a weekly podcast interviewing sales reps turned entrepreneurs through buying or building businesses. This newsletter is a curated bi-weekly list of my favorite content, events, and business ideas, and celebrates bonus Salespreneur Stories! To see how I got started go here.

Making your first $1 online

I wish I had a picture from this day!

In my most recent episode with Tom Alaimo, we talked a lot about the importance of making your first dollar online. It’s a turning point as an entrepreneur when you turn nothing into something that puts money in your pocket!

One of the best things that I did was publicly document my entire journey on LinkedIn. I’m not an influencer or expert, but I was a sponge and wanted to share everything I was learning. Things like events I put on, milestones, promotions, lessons learned, and industry insights. This became an incredible networking tools and built credibility with my peers online.

I was one of the first sales reps hired at a startup. We went from under $1M in revenue to 40x growth and dominated the restaurant tech vertical in 2 years.

This personally blessed me when the team led got caught in a layoff. (not fun stuff)

I wrote an article “3 Things I learned at a hyper-growth startup” to share my story.

2 weeks later, a CEO of a startup selling to the same space hit me up on LinkedIn.

“We are expanding our sales team and your profile looks solid and aligns with our GTM, so directly reaching out to you for a quick 30 mins call.”

The CEO & VP of Sales were interested in selling to franchisee’s and wanted to get their first few customers by contracting me to do some sales. I brought on a former executive to partner on the deal since it’d be my first time doing this.

Deal Structure

Services

Develop playbook on “How to sell to franchisees”
Prospecting and closing deals
Determine pricing & packaging
Help find product marketing fit/ ideal customer profile

Compensation:

$80/hr
10% commission

My Results

21 meetings held
~$250k of pipeline
65 hours (4 weeks)
Scraped 1,000’s of leads

What I learned

Fractional work provides massive value

Hiring full-time employees is a massive commitment for a company. Contractors that can solve a specific problem for a fraction of the time/pay are game changers.

Managing Expectations

Your first contract is always a learning experience.

My impression was that they wanted me to help them learn how to sell it and they expected me to be a remote closer. This was challenging because this was a totally new vertical for them and they wanted me to build it out for them.

2 things I would do different…

(1) I’d switch my contract to be fully based on booking meetings and training the VP of Sales to close the deals, instead of me. This would have given me more control over my success.

(2) Build a case study from this and prospect similar startups to support fractionally

Stuff I hope you like…..

Salespreneur Milestones

“Instead of baby showers, let’s host business shower. When a friend starts a business, we all come together, and congratulate them and bring resources for their business.” - Elon Musk