Family Businesses with Josh Trim
Join Jake Voll as he sits down with Josh Trim of Pennington & Trim to talk about what it takes to grow a security company across generations — and why “sales” isn’t about pressure or commissions, it’s about trust, character, and delivering the right solution for the customer.
In this episode, Jake and Josh unpack the early grind of building a company, the advantage technical people often have in sales, and the mindset shift that separates short-term transactions from long-term customers. Josh shares the principles he learned from his dad (industry legend Ed Trim) and the day-to-day habits that build credibility fast — especially when you’re young and trying to earn respect in a tough trade.
In this episode, we talk about...
In this episode, we talk about...
✅ Why technical people often make the best sales reps in security
✅ The “early grind” reality of starting and scaling a security business
✅ How selling the right solution creates long-term customers (and referrals)
✅ The character-first mindset that builds trust faster than product knowledge
✅ Josh’s best advice for younger leaders: outwork everyone, show up early, earn respect
✅ Why caring about the customer beats caring about commissions (and improves close rates)
✅ The “early grind” reality of starting and scaling a security business
✅ How selling the right solution creates long-term customers (and referrals)
✅ The character-first mindset that builds trust faster than product knowledge
✅ Josh’s best advice for younger leaders: outwork everyone, show up early, earn respect
✅ Why caring about the customer beats caring about commissions (and improves close rates)
Coffee Break With Jake is recorded live every Friday at 11am ET. Join us live or register to attend at https://go.ssandsi.com/coffeebreak
