Friday 15 Podcast

Can You Build a Successful Career at a Family-Owned B2B Company?

Brian Beck and Andy Hoar welcome Trent Guyer from Grasshopper Mowers to discuss building an ecommerce career at a third-generation family-owned manufacturer.

Friday 15 Podcast · Guest: Trent Guyer, VP of Marketing and Digital Strategy, Grasshopper Mowers

Key takeaways

  • According to the Census Bureau, 90% of businesses in the United States are family-owned or controlled, but a PWC survey found only 39% of family-owned businesses consider themselves to have strong digital capabilities.
  • A Master B2B LinkedIn poll found 88% of practitioners believe it is possible to build a successful ecommerce career at a traditional family-owned B2B company.
  • Shopify CEO Toby Lutke announced employees must prove jobs cannot be done by AI before asking for more headcount, with AI usage factored into performance reviews.
  • Trent Guyer cited brand protection as the most compelling argument for Amazon: showing leadership that inferior Chinese-made parts were being sold under their brand name shifted the conversation.
  • Two-thirds of Grasshopper's online orders come outside standard dealership hours, and the average customer drive distance to a dealer is 70 miles round trip, demonstrating ecommerce fills genuine gaps.

Shopify requires AI justification for hiring

Shopify CEO Toby Lutke announced employees must prove jobs cannot be done by AI before asking for more headcount. AI usage will be factored into performance reviews. The hosts confirmed this is real, with hiring held up pending AI capability assessment. Google reported about a third of their code was being written by AI a year ago, likely closer to 40 to 50% now. Tech companies are leading this shift, but the hosts predicted it will spread across industries.

These guys said the quiet part out loud. Tech companies are sort of on the bleeding edge here. This is real. And I think this is going to spread across a lot of companies.

Andy Hoar, Master B2B

Family-owned business landscape

According to the Census Bureau, 90% of businesses in the United States are family-owned or controlled. However, a PWC survey found only 39% of family-owned businesses consider themselves to have strong digital capabilities. This creates a question for ecommerce professionals: can you build a successful career in this environment, or will family dynamics and conservative culture limit growth?

Introducing Grasshopper Mowers

Trent Guyer, VP of Marketing and Digital Strategy at Grasshopper Mowers, joined to share his experience as a third-generation family member. His grandfather started with portable grain dryers, then shifted to zero-turn mowers around 1980 when the farm market weakened. Today Grasshopper sells to government institutions, schools, cities, commercial operators, and large-acreage homeowners. Their mowers even cut the grass at the White House.

The Amazon argument

Channel conflict was the primary concern when Guyer proposed selling on Amazon. Dealers felt the company would sell around them or behind their backs. The breakthrough came when Guyer showed second-generation leadership that inferior Chinese-made transmissions were being sold on Amazon under the Grasshopper name. Brand protection became the compelling argument. Prices are set slightly higher than dealers, and dealers still offer same-day availability.

Data supported the case

Research showed two-thirds of online orders came outside standard dealership operating hours. Dealers are typically closed evenings and Sundays. The average customer drive distance to a dealer is 70 miles round trip. Grasshopper equipment is durable and often resold through multiple owners who may not know their local dealer. These gaps in traditional coverage demonstrated ecommerce captures incremental sales rather than cannibalizing dealer revenue.

When have I ever done anything that was a detriment to the company? I have the same feelings you do. I would never make a decision like that.

Trent Guyer, Grasshopper Mowers

Career advice for non-family members

Guyer’s advice for non-family employees: patience. Digital transformation at a family-owned company may take a decade rather than months. If you are using the company as a stepping stone, the relationship will not work. But if you prove trustworthiness and demonstrate genuine care, family-owned businesses provide deep loyalty in return. The open-door culture at Grasshopper means anyone can talk to leadership about any topic.

Poll results

A LinkedIn poll asked whether it is possible to build a successful ecommerce career at a traditional family-owned B2B company. Results showed 88% said yes, while 12% said no. Guyer suggested the 12% may perceive family-owned businesses as slow movers with dated technology. But he reframed this as stability: older internal systems have lasted longer than many vendors, and investment focuses on manufacturing efficiency where seconds matter.

Frequently asked questions

Can you build a successful ecommerce career at a family-owned B2B company?

A Master B2B LinkedIn poll found 88% of practitioners said yes, it is possible to build a successful ecommerce career at a traditional family-owned B2B company. The 12% who said no may perceive family-owned businesses as slow movers with dated technology. Trent Guyer, a third-generation family member at Grasshopper Mowers, recommended patience and proving trustworthiness over time rather than expecting rapid change.

How did Grasshopper overcome channel conflict concerns with Amazon?

Trent Guyer said brand protection was the most compelling argument. When he showed second-generation leadership that inferior Chinese-made transmissions were being sold on Amazon under the Grasshopper name, the conversation shifted from whether to sell online to how quickly they could get their genuine products listed. Prices are set slightly higher than dealer prices, and dealers still offer same-day availability that Amazon cannot match.

What data supported ecommerce investment at Grasshopper?

Trent Guyer's research found two-thirds of online orders came outside standard dealership operating hours, when dealers are closed evenings and Sundays. The average customer drive distance to a dealer is 70 miles round trip. These gaps in traditional channel coverage demonstrated that ecommerce captures incremental sales rather than cannibalizing dealer revenue.

What is Shopify's new AI policy for hiring?

Shopify CEO Toby Lutke announced employees must prove jobs cannot be done by AI before asking for more headcount. AI usage will be factored into performance reviews. The hosts noted that tech companies are leading this shift, with Google reporting about a third of their code was being written by AI a year ago, likely closer to 40 to 50% now. This trend will spread beyond tech companies.

Why do family-owned businesses stay private?

Trent Guyer explained that manufacturing provides flexibility and ongoing opportunity. Grasshopper can cut steel, machine, fabricate, powder paint, weld, and do final assembly. If market conditions changed dramatically, they could become a job shop for other manufacturers. Selling to private equity provides a one-time payout, while continued ownership allows the family to keep building value across generations.

What advice does Trent Guyer have for non-family employees?

Patience is essential. Digital transformation at a family-owned company may take a decade rather than months or years. If you are using the company as a stepping stone without long-term commitment, the relationship will not work. But if you prove trustworthiness and demonstrate care for the company, family-owned businesses tend to provide deep loyalty in return, riding with employees through challenges.

Sources & methodology

  1. Friday 15 Podcast, Master B2B
  2. Master B2B LinkedIn poll, April 2025
  3. Trent Guyer, Grasshopper Mowers
  4. US Census Bureau, family-owned business statistics
  5. PWC, family-owned business digital capabilities survey
  6. Shopify CEO announcement on AI hiring policy
Andy Hoar Andy Hoar
Co-Founder, Master B2B

Andy is a Co-Founder of Master B2B, founder of Paradigm B2B and author of the book Bot2Bot: The New Future of B2B Commerce. Andy is one of the leading global authorities on B2B commerce strategy.

Brian Beck Brian Beck
Co-Founder, Master B2B

Brian is a co-founder of Master B2B, Managing Partner of Amazon agency Enceiba, and author of the book "Billion Dollar B2B Ecommerce." Brian has also been C-level digital commerce executive with two decades of experience.

New: B2B Exchange at Shoptalk Presented by Master B2B

X