Because of Sales

Play your sales career like this to win long-term - Jake Pastick


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In this episode of Because of Sales, Dylan sits down with Jake Pastick, a seasoned sales professional who’s worked across early-stage startups, Fortune 500 marketing agencies, private equity environments, and the high-ticket remote closing world. Jake shares his unconventional path from college basketball at Davidson, to corporate sales, to freelancing, and ultimately designing a sales career optimized for return on time, autonomy, and long-term fulfillment.


They dive deep into the realities of W2 vs 1099 sales, why “job security” is often an illusion, how to build leverage as a salesperson, and what it actually takes to survive (and thrive) in high-ticket sales long term. Jake also breaks down consistency vs peak performance, career optionality, and why perspective—not talent—is the ultimate edge in sales.

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