Jun 15, 2023 · 34m · american-optimist
Ep 62: Ben Rubenstein Says Resumes Are Useless; Here's How to Find the Best Salespeople · Joe Lonsdale
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of American Optimist, host Joe Lonsdale interviews serial entrepreneur Ben Rubenstein about his journey founding Yodel, OpCity, and Setpoint. They discuss unconventional sales hiring, the dynamics of corporate acquisitions, PropTech innovation, and community advocacy through foster care leadership.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Joe holds 20.7% of the talking time here. How this is scored →
Joe as informed peer 3.6 Guest teaching 3.1 Guest disagreement 0.9 Joe pushing back 1.6
speaking balance: gold is Joe, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 17:02 Pushing back on platform bullying framing
When Joe suggests that large platforms had extreme leverage and could force OpCity to sell, Ben counters that OpCity was actually their largest customer and choosing to sell was about strategic focus.
Hardest push from Joe ▶ 9:06 Challenging inside sales over in-person sellingJoe challenges Ben's preference for phone sales, arguing that face-to-face visits establish far superior trust with local business owners.
Biggest teaching moment ▶ 8:07 The reality of 99 percent sales rejectionBen breaks down the reality of high-volume sales, explaining why a 1 percent conversion rate makes attitude and resilience vastly more predictive of success than traditional resumes.
Joe holds their own ▶ 16:31 Platform dependency and aggregator leverageJoe demonstrates deep industry insight by highlighting the existential platform risk of building on top of dominant aggregators who inevitably seek to capture all downstream value.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Joe as informed peer | Guest teaching | Guest disagreement | Joe pushing back | Why |
|---|---|---|---|---|---|---|
| Early Entrepreneurial Beginnings and Value-Based Pricing | 3 | 2 | 1 | 1 | Joe asks friendly introductory questions about Ben's early childhood candy business and the founding of Yodel. The tone is casual and conversational with Joe probing slightly into pricing competition. | |
| Building Sales Teams and the Key Traits of Great Salespeople | 3 | 5 | 1 | 2 | Ben details his core hiring criteria and explains why resumes and college degrees are unhelpful in sales. Joe questions whether inside sales outperforms in-person visits, allowing Ben to explain efficiency and conversion math. | |
| Yodel Acquisition by Web.com and Cultural Lessons | 4 | 2 | 0 | 1 | Ben and Joe analyze what went wrong culturally after Yodel was acquired by Web.com. Joe contributes his own commentary on how large corporate acquisitions often absorb and dissolve startup cultures. | |
| OpCity's Rapid Growth and Innovative Real Estate Model | 4 | 4 | 2 | 2 | Ben explains OpCity's business model and its real-time lead dispatch algorithm, comparing it to Uber versus Match.com. Joe presses on platform dependency and leverage from large aggregators like Zillow and Realtor.com. | |
| Startup Alignment versus Big Company Leadership Challenges | 4 | 3 | 1 | 2 | Ben outlines his new venture Setpoint and how PropTech models shift between bull and bear housing markets. Joe interjects with questions comparing alternative models like Opendoor and playfully comparing housing values. | |
| Philanthropic Work with CASA and Supporting Foster Children | 3 | 4 | 0 | 1 | Ben shares his 11 years of volunteer work with CASA assisting abused and foster children. Joe listens intently and asks how institutional policy and incentives can be reformed to break generational trauma. | |
| Reasons for Optimism, AI in Sales Coaching, and Conclusion | 4 | 2 | 1 | 2 | The conversation closes with an optimistic view of US entrepreneurial culture and the role of AI in workforce upskilling. Ben reframes Joe's question on AI sales coaching by distinguishing diagnostic feedback from human emotional motivation. |
Statements from this episode (13)
Rubenstein notes the Yellow Pages was a $20 billion market in 2005
“We saw the yellow pages in the 2005 was a twenty billion dollar market.”
Yellow Pages ads used to cost local businesses $10,000 a month
“Those ads in the yellow pages were really expensive. It would be 10,000 dollars a month for a full page ad for like a plumber.”
Attitude is the most vital sales trait due to constant rejection
“And finally, by far and away, the most important characteristic was their attitude. This is a job, which was just constant rejection and you know, our best salespeople, you know, people, most salespeople are making an, especially when we're on the phone, a 102…”
Inside sales teams proved easier to scale and manage than outside sales
“The inside salespeople, it was easier to scale, easier to manage, and could be much more productive.”
In-person sales achieved higher close rates and order sizes than phone sales
“The close rate was higher of people in person, right? Actually, the order size was actually higher as well.”
Online advertising and social media for small businesses have become commodities
“Now pretty much every small business owner understands what social media is and online advertising and reputation management. So I think it made a lot of sense at the time, but and today it's very, very important. It's just more of a commodity today.”
Rubenstein found college experience negatively predicted success in phone sales hires
“Actually we found that college experience was a negative.”
OpCity connected with prospective homebuyers online in under four seconds
“Our average connect time was less than four seconds.”
Rubenstein calls homeownership the single biggest unlock to wealth in America
“I mean, homeownership is the biggest unlock to wealth in our country. It's one of the most important things in communities in our country that we have more people who own homes.”
PropTech demand shifted from cash offers to buy-before-you-sell bridge financing
“Now that product is pretty much dried up because people don't need that anymore. Well, there's just not as many offers on any property, right? But the products that have really taken off now are buy before you sell because previously you didn't need buy before…”
Parents in the child protective system were usually in it as kids
“The scariest pattern of all of them is the parents in the CPS system were usually kids in the CPS system.”
Future workers will juggle multiple professions, not just multiple jobs
“I think the future is going to be, we all have not only work at many companies, but we have many different professions, because technology's changing so rapidly.”
AI will diagnose employee performance, but human leaders must provide motivation
“I don't think AI is going to be able to motivate you. I think there's going to be great leaders that are going to, well, maybe it will be able to motivate you, but I think AI will be great at diagnosing where you need to improve. So I think that combination of…”