Dec 5, 2023 · 38m · we-live-to-build
Turn Your Self Audio Down and Watch Everything Change
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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 in-depth interview, entrepreneur and mentor Jeremy joins host Sean Weisbrot to dissect the psychological foundations of startup success, emphasizing purposeful resilience, scientific founder evaluation, and the mastery of interpersonal communication. Together, they critique conventional venture capital models while providing actionable frameworks for active listening, customer-centric growth, and personal alignment.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Sean holds 34.4% of the talking time here. How this is scored →
Sean as informed peer 3.7 Guest teaching 4.7 Guest disagreement 1.6 Sean pushing back 2.6
speaking balance: gold is Sean, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 32:22 Firm rejection of macroeconomic mindset shift
Jeremy flatly dismisses Sean's premise that COVID fundamentally transformed investor mindsets, asserting adjustments were merely superficial financial and P&L reactions.
Hardest push from Sean ▶ 10:16 Direct challenge on judging knowledge versus coachabilitySean explicitly questions whether Jeremy's 60-second assessment of existing founder knowledge is unfair compared to assessing their patience and coachability.
Biggest teaching moment ▶ 8:24 Detailed micro-expression assessment methodologyJeremy educates Sean on how he evaluates listening eyes, tone of voice, and micro-expressions at a millimeter level across hundreds of cross-cultural calls.
Sean holds their own ▶ 27:43 Host deconstructs VC misaligned incentivesSean demonstrates domain knowledge by detailing how institutional venture capital forces founders into valuation fixation over customer value, justifying his angel investing approach.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Sean as informed peer | Guest teaching | Guest disagreement | Sean pushing back | Why |
|---|---|---|---|---|---|---|
| Discovering Passion and Purpose Through Life Exploration | 2 | 4 | 1 | 2 | Sean asks broad exploratory questions regarding founder psychology and clarity exercises. Jeremy defines the concept of the discovery phase and the quantified must-have why required to endure founder challenges. | |
| Building Resilience and Uncovering Blind Spots | 4 | 4 | 2 | 4 | Sean pushes back on Jeremy's framing by clarifying his question and sharing a personal ping pong anecdote to argue that seeking mentors directly rarely works. Jeremy counters by outlining the seed traits and execution speed mentors look for in high performers. | |
| Reading Micro-Expressions and Evaluating Processing Speed | 2 | 6 | 2 | 1 | Sean asks how to evaluate seed traits without long observation periods. Jeremy delivers an extensive breakdown of assessing eye movement, micro-expressions, and cognitive processing speed based on conducting over 900 calls in 90 days. | |
| Balancing Baseline Expectations with Founder Coachability | 6 | 4 | 2 | 5 | Sean directly challenges whether judging founders on pre-existing knowledge is unfair compared to assessing coachability, drawing on his own founder advisory experience. Jeremy defends his screening mechanisms while Sean details his structured audit documents. | |
| The Two Percent Daily Communication Improvement Rule | 5 | 3 | 1 | 3 | Jeremy shares his algorithmic rule of improving communication two percent daily through frequent failure. Sean offers a contrasting personal philosophy centered on genuine cultural curiosity and shared life experiences. | |
| Mid-Show Interlude and Channel Subscription Call to Action | 2 | 5 | 1 | 1 | Following a mid-episode subscription interlude, Sean asks how founders sustain daily stamina. Jeremy reframes burnout as a lack of alignment rather than time expenditure, asserting business should always serve human desires. | |
| Customer Retention, Growth Multiples, and the Drive for IPOs | 4 | 5 | 1 | 3 | Sean questions why society treats going public as the primary success metric when bootstrapped founders are often happier. Jeremy outlines LP return requirements, the timer imposed by VC money, and founder status incentives. | |
| Venture Capital Dynamics and Power Law Versus Angel Investing | 6 | 5 | 2 | 4 | Sean critiques venture capital for distracting founders from customer value in pursuit of valuation metrics, highlighting his preference for angel investing. Jeremy agrees and elaborates on the flaws of power law fund models versus scientific evaluation. | |
| Macroeconomic Shifts and the Persistence of Power Law Mindsets | 3 | 6 | 3 | 2 | When Sean asks if macroeconomic shifts like COVID have fundamentally altered investor thinking, Jeremy firmly disagrees and explains that industry changes have remained superficial rather than addressing founder evaluation methods. | |
| Turning Down Self Audio to Enhance Interpersonal Connection | 3 | 5 | 1 | 1 | Jeremy summarizes his core philosophy of turning down internal self audio to focus empathetically on nonverbal cues and others' needs. Sean recommends Charisma on Command as a complementary resource before wrapping up. |
Statements from this episode (16)
Barr: Founders Should Seek Emotional Extremes, Not Average Feelings, During Discovery
“Feel where you feel really, really strong emotions and really, really negative emotions. And don't really go towards the things that are just like, ah, I feel average about it. You want to have really, really strong emotions for things that are really, really …”
Jeremy Barr: Founder Resilience Requires a Quantified 'Must-Have Why'
“Your resilience comes from your, what I would say your, is your quantified must have why I must have this in life. And if you don't have a thing that you must have in life, you're not going to have that resilience to deal with all that you have to deal with.”
Barr: High-performing founders execute 5-8 weekly tasks versus one for beginners
“The high performers get it done by next week. And they get like five or eight things done. I can usually give them a lot more actions. Versus a more beginner person or somebody who is not as absorbent will take three or four weeks to get one thing done.”
Barr: The first 60 seconds of a video call predict founder competence
“There's a ton of things that you can tell in the first 60 seconds of a call about somebody, and it's very, very predictive. It's not a guessing game.”
Barr: Founder Coaching Must Fit Within a 60-to-90-Day Investability Timeline
“Because at the end of the day, you still don't want, even if you're trying to grow somebody, For them to have 300 things that are gonna take them a year for you to teach them through when you need them. You know, productive or investable in 60 days or 90 days.”
Jeremy Barr: Founders Should Expect a 99% Rejection Rate and Need Volume
“So, you know, 99% of people are ignoring ads in the world, which kind of transposes to when you're approaching interview investors and any sort of new thing in general is that you're supposed to have like a 99% failure rate, and so this concept of volume, goin…”
Jeremy Barr: Listening Is the Top Trait for Founder Investability
“Listening is probably the number one trait I'm always looking for because it applies to Pretty much everything for you to become like a gravity ball, which is my investable thesis. Is that gravity ball, your ability to communicate to and relate to a wide varie…”
Barr: 6% Monthly Growth Over 7-Year IPO Timeline Yields $133 Million
“So if you take a company at one million dollars and you have them grow six percent month over month for the seven year median to IPO time, you get one hundred thirty three million dollars.”
Barr: Conversation success relies on duration and follow-up desire
“You, the grading metric generalized is one conversation duration. Two, conversation follow up. If they want to talk to you a second time, that's an extremely good sign. So if you had a first meeting and they want a second meeting, great. So those are the two g…”
Jeremy Barr: Burnout is not driven by time and energy input
“Burnout is not a function of time and energy like a lot of people think.”
Jeremy Barr: Work-life balance is a nine-to-five mindset
“Work-life balance is a nine-to-five mindset, and I don't say that in a bad way, I just say it's a context way.”
Barr: Media buying can scale revenue to $50M without product repeatability
“It's crazy how, if you get really good at media buying and sales pages, you can actually get over fifty million and you're in the top six percent of companies and you still don't have repeatability or investability.”
Barr: Most founders should bootstrap or raise from angels rather than VCs
“And I'm a VC and I don't recommend a lot of people go VC. I do recommend people go bootstrap, or if you're not going to bootstrap and you want a little bit of money, go angel.”
Barr: Taking venture capital too early puts startups on an aggressive funding timer
“The problem is in application, when you're given money too early before you maybe got your product market fit or other key customer listening metrics you are then trying to accelerate, because once you give the money, it's a timer. You have to get a return on …”
Barr: Founder seed evaluation is a science, not power-law guesswork
“I don't think that, I think you can actually understand companies at a seed level and founders at a seed trait level and understand, do they have the communication? Do they have listening? Do you have the, all these things that are going to make them successfu…”
Weisbrot: VC power-law investing is just bad money management hiding failure
“I have heard some of those ideas that you just assume most of the companies are going to fail. And I feel like that's just bad, like money management being kind of swept under the rug. So that's why I like to do angel investing because I'm going to do everythi…”