IN THIS EDITION
Coming to you live with our MJ edition (#23)
Like Mike in the NBA finals, BoS subscribers won’t be losing anytime soon.
Here’s what you can expect from us today:
From welfare to wellbeing through a career in sales - Tristan Workman
10 ChatGPT prompts to run better discovery
Master small talk with high-net worth individuals
And more…
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LIVE FROM THE SALES FLOOR
Recent Events
Trump just passed new H-1B payment of $100k for immigrants (X)
DOJ gives this sales rep prison time for healthcare fraud (YCJ)
Tips + Tricks
The best way to engage an narcissist (LinkedIn)
Use these 10 ChatGPT prompts to prep for a discovery call (LinkedIn)
Other Stuff
How to handle prospects who ask for discounts (X)
Ranked: How B2B companies want to be contacted by sellers (LinkedIn)
Discussion: Do experienced sales people want to sell forever? (Reddit)
OUR SPONSOR
This week’s sponsor is The Serial Sales Community.
Are you familiar with the game, two truths and a lie?
The game where you share three “truths” to someone, and the other person has to guess which one of the three is actually a lie.
As if it weren’t self explanatory enough.
Let’s play.
Truth 1: There were 300 open 1099 remote sales jobs shared last month in TSSC.
Truth 2: We work with people to secure these roles with all levels of varying sales experience (including none).
Truth 3: This 1099 remote sales space is booming at a rate never seen before.
Take a few seconds if you need it…
Three… two… one…
The lie was “Truth 1”.
Because we actually shared 470 open 1099 remote sales roles last month inside TSSC.
You’re not finding these roles on LinkedIn, Indeed, or Glassdoor.
You find them inside The Serial Sales Community.
If you’d like to inquire, you can apply with the team here.
Mention Because of Sales for 5% off any membership you choose.
Now back to the newsletter
SELLER’S SECRETS
Who is Tristan Workman, and what is he up to?
Now (recently) based in Austin, TX, Tristan is a high-ticket remote sales professional and sales team leader helping top-tier coaching programs scale to 7 and 8 figures.
Check out Tristan’s full interview on Youtube, Spotify, or Apple Podcasts.
Tristan’s come up (in 10 bullet points)
Worked 40+ hours weekly in high school service jobs
Studied finance at UNC Wilmington, graduated in 2020
Rejected 9-5 path for commission-based sales
Moved to Tennessee to join a friend's construction startup
Built sales chops selling decks and roofs via self-generated leads
Discovered remote closing through a friend in Amazon FBA
Balanced in-person and online sales calls daily from Starbucks
Invested in his first course: Sales Sniper Bootcamp
Left construction after cashflow issues and fulfillment failures
Landed on an A+ remote offer and closed $1M+ in a month with full conviction
If Tristan had a catchphrase, it’d be “you can go a lot further than you think”. He recently completed an Ironman with only one week of training prior.
Tristan’s sales alpha and best practices
1: Obsess over an opportunity that allows conviction-based selling
Tristan refuses to sell anything he doesn’t believe in. After facing burnout selling for low-integrity business owners, vetting opportunities for legitimacy is priority A1. He asks founders to show results, connect him to clients, and prove their sales team’s earnings before committing.
This radical conviction translated to a 60% offer-to-close rate when he aligned with top-tier founders like Dickie Bush and Nicolas Cole.
2: Try the “hammer them” strategy to eliminate objections
Tristan implemented a version of Jeremy Haynes' "hammer them" email strategy, sending 6 targeted emails before a call. Each email tackled a specific concern: price, credibility, proof, differentiation. This indoctrinates the lead before the closer even introduces themselves, making the sales call smoother and reducing refund/buyer remorse rates.
3: Leverage custom intro videos at scale to land the role you want
Tristan broke into high-ticket sales by DM'ing 100+ creators with personalized Loom videos. He stands out by making them high-quality, direct, and conviction-driven. One DM to Dickie Bush at 3 AM led to him joining the team and helping them break $1M in a month.
He now encourages reps to approach outreach like sales calls: tailored, persuasive, and professional.
4 things to steal, 4 tips to implement:
Don’t fall for the "laptop lifestyle" myth
Making $30K/month requires 10-14 calls/day
Sales is hard work, not passive income
Expect long hours and repetitive effort
Most flashy closers are over-leveraged
Master the first impression like your life depends on it
Your first impression is the most critical part of any relationship.
When applying for a role, create a personalized, high-quality Loom video.
Show energy and enthusiasm; demonstrate you are the right person for the job.
Don't send generic, low-effort applications.
Develop a "cashier" sales process
Automate content with answers to common objections before the call.
Use a "pre-call hammer them sequence" to educate prospects.
Turn your closers into "cashiers" by removing objections early.
Shift the conversation from objection-handling to a collaborative discussion.
Obsess over "speed-to-lead" to win more business
Respond to leads as quickly as possible when they come in.
The faster you get on the phone, the more they appreciate it.
Speed to relationship builds trust and earns business.
The most known and fastest to respond product often wins.
Connect with Tristan
Check out Tristan’s full interview on Youtube, Spotify, or Apple Podcasts.
BEFORE YOU GO
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