Running the business
Should I hire someone to sell newsletter ads before selling them myself?
Short answer
No. Sell it yourself first. I paid a cold-calling contractor about $16,000 to sell ads for my insurance newsletter and got nothing. Once you've done the hard part yourself, you know what to hire for, and that's when a commission rep changes everything.
Hiring help before you've done the process yourself costs real money for nothing. I have the $16,000 receipt.
Doing the hard selling personally is what makes you a good manager of salespeople later. You learn the objections, the price that closes, and which businesses say yes.
When hiring does work
After you know the motion, a rep is the best money you'll spend. One operator hired a commission rep at 25% and got to $25,000 a month. Another made very little for four and a half years, hired a salesperson around 22 years old, and hit $25,000 in a month.
Where not to hire
Upwork, for a committed role. Freelancers there are gig workers who don't want one employer, and nobody strong on my team came from Upwork. I had a hire quit the day after onboarding. The red flag was there early: the candidate could only work until 2pm when the posting said the hours were non-negotiable. Hire from places where people want one full-time job.
Answered by TJ Larkin. From operator and team calls in May and June 2026. Rep results are other operators', as TJ relayed them. Last updated .