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  • 😎 3x'd his income closing $10M, ChatGPT prompts for better discovery, how to sell to people with money

😎 3x'd his income closing $10M, ChatGPT prompts for better discovery, how to sell to people with money

Despite all odds, Tristan has created his dream life through remote closing.

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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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.

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