StarZero All shows Try the podcast clipper →

May 17, 2019 · 31m · 20vc

20VC: How To Build True Human Relationships with VC Pre-Investment, Why Valuation Is Not The Only Term and When To Take Lower Offers & How To Approach Mental Health As A Founder with Jon Dishotsky, Founder & CEO @ Starcity

Jon Dishotsky · 18m spoken Harry Stebbings · 10m spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

In this episode of The 20 Minute VC, Harry Stebbings interviews Jon Dishotsky, founder and CEO of Star City, about building co-living solutions for urban housing unaffordability. Dishotsky discusses key lessons from Y Combinator, fundraising strategies that prioritize partner chemistry over top valuation, and actionable practices for maintaining founder mental health.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 37.9% of the talking time here. How this is scored →

Harry as informed peer 2.7 Guest teaching 2.3 Guest disagreement 1.0 Harry pushing back 1.9
05100:0010:0020:0030:004:05–6:43 · Harry as informed peer 1/10 Jon Dishotsky's Background and Founding of Star City Harry opens with a warm, supportive introduction asking about Jon's background and the origin story of Star City. Jon responds warmly, praising Harry's hustle and sharing his personal background growing up around multi-generational housing in Palo Alto.6:43–11:03 · Harry as informed peer 5/10 PropTech Evolution and Asset-Heavy VC Fundraising Harry takes on a contrarian VC perspective, challenging Jon on why an investor shouldn't immediately dismiss Star City as an undesirable asset-heavy business model. Jon defends the model by walking through their customer research, MVP validation, and encouragement from Y Combinator.11:04–15:06 · Harry as informed peer 3/10 Key Learnings from Y Combinator for Founders Harry inquires about learnings from Y Combinator and when a founder should accept a lower valuation. Jon explains why quibbling over seed valuations is shortsighted compared to choosing aligned long-term board partners.15:06–17:08 · Harry as informed peer 5/10 Building Long-Term Relationships vs. Transactional Fundraising Harry strongly challenges the trend of compressed two-week fundraising sprints, calling it crazy to select ten-year board members in days. Jon wholeheartedly agrees, elaborating on how continuous relationship building beats transactional fundraising.17:10–21:23 · Harry as informed peer 1/10 Founder Mental Health, Self-Care, and Daily Gratitude Harry asks why founders neglect mental health, prompting Jon to share insights from his father, a psychiatrist, while calling out Silicon Valley hustle porn. Harry playfully accepts Jon's advice on therapy, exercise, and gratitude journaling.21:24–24:07 · Harry as informed peer 2/10 Perspective, Humility, and the Advantages of Seasoned Founders Harry asks about the advantages of seasoned founders. Jon outlines how family life provides a daily mental reset and how mid-thirties maturity fosters humility and reduces ego-driven decision making.24:07–27:24 · Harry as informed peer 2/10 Quickfire Round and Future Vision for Star City Harry runs through a quickfire round covering books, tech industry changes, and investor relationships. Jon challenges conventional fundraising advice and articulates Star City's vision to make major cities accessible.4:05–6:43 · Guest teaching 1/10 Jon Dishotsky's Background and Founding of Star City Harry opens with a warm, supportive introduction asking about Jon's background and the origin story of Star City. Jon responds warmly, praising Harry's hustle and sharing his personal background growing up around multi-generational housing in Palo Alto.6:43–11:03 · Guest teaching 3/10 PropTech Evolution and Asset-Heavy VC Fundraising Harry takes on a contrarian VC perspective, challenging Jon on why an investor shouldn't immediately dismiss Star City as an undesirable asset-heavy business model. Jon defends the model by walking through their customer research, MVP validation, and encouragement from Y Combinator.11:04–15:06 · Guest teaching 3/10 Key Learnings from Y Combinator for Founders Harry inquires about learnings from Y Combinator and when a founder should accept a lower valuation. Jon explains why quibbling over seed valuations is shortsighted compared to choosing aligned long-term board partners.15:06–17:08 · Guest teaching 1/10 Building Long-Term Relationships vs. Transactional Fundraising Harry strongly challenges the trend of compressed two-week fundraising sprints, calling it crazy to select ten-year board members in days. Jon wholeheartedly agrees, elaborating on how continuous relationship building beats transactional fundraising.17:10–21:23 · Guest teaching 4/10 Founder Mental Health, Self-Care, and Daily Gratitude Harry asks why founders neglect mental health, prompting Jon to share insights from his father, a psychiatrist, while calling out Silicon Valley hustle porn. Harry playfully accepts Jon's advice on therapy, exercise, and gratitude journaling.21:24–24:07 · Guest teaching 2/10 Perspective, Humility, and the Advantages of Seasoned Founders Harry asks about the advantages of seasoned founders. Jon outlines how family life provides a daily mental reset and how mid-thirties maturity fosters humility and reduces ego-driven decision making.24:07–27:24 · Guest teaching 2/10 Quickfire Round and Future Vision for Star City Harry runs through a quickfire round covering books, tech industry changes, and investor relationships. Jon challenges conventional fundraising advice and articulates Star City's vision to make major cities accessible.4:05–6:43 · Guest disagreement 0/10 Jon Dishotsky's Background and Founding of Star City Harry opens with a warm, supportive introduction asking about Jon's background and the origin story of Star City. Jon responds warmly, praising Harry's hustle and sharing his personal background growing up around multi-generational housing in Palo Alto.6:43–11:03 · Guest disagreement 2/10 PropTech Evolution and Asset-Heavy VC Fundraising Harry takes on a contrarian VC perspective, challenging Jon on why an investor shouldn't immediately dismiss Star City as an undesirable asset-heavy business model. Jon defends the model by walking through their customer research, MVP validation, and encouragement from Y Combinator.11:04–15:06 · Guest disagreement 1/10 Key Learnings from Y Combinator for Founders Harry inquires about learnings from Y Combinator and when a founder should accept a lower valuation. Jon explains why quibbling over seed valuations is shortsighted compared to choosing aligned long-term board partners.15:06–17:08 · Guest disagreement 1/10 Building Long-Term Relationships vs. Transactional Fundraising Harry strongly challenges the trend of compressed two-week fundraising sprints, calling it crazy to select ten-year board members in days. Jon wholeheartedly agrees, elaborating on how continuous relationship building beats transactional fundraising.17:10–21:23 · Guest disagreement 1/10 Founder Mental Health, Self-Care, and Daily Gratitude Harry asks why founders neglect mental health, prompting Jon to share insights from his father, a psychiatrist, while calling out Silicon Valley hustle porn. Harry playfully accepts Jon's advice on therapy, exercise, and gratitude journaling.21:24–24:07 · Guest disagreement 0/10 Perspective, Humility, and the Advantages of Seasoned Founders Harry asks about the advantages of seasoned founders. Jon outlines how family life provides a daily mental reset and how mid-thirties maturity fosters humility and reduces ego-driven decision making.24:07–27:24 · Guest disagreement 2/10 Quickfire Round and Future Vision for Star City Harry runs through a quickfire round covering books, tech industry changes, and investor relationships. Jon challenges conventional fundraising advice and articulates Star City's vision to make major cities accessible.4:05–6:43 · Harry pushing back 0/10 Jon Dishotsky's Background and Founding of Star City Harry opens with a warm, supportive introduction asking about Jon's background and the origin story of Star City. Jon responds warmly, praising Harry's hustle and sharing his personal background growing up around multi-generational housing in Palo Alto.6:43–11:03 · Harry pushing back 5/10 PropTech Evolution and Asset-Heavy VC Fundraising Harry takes on a contrarian VC perspective, challenging Jon on why an investor shouldn't immediately dismiss Star City as an undesirable asset-heavy business model. Jon defends the model by walking through their customer research, MVP validation, and encouragement from Y Combinator.11:04–15:06 · Harry pushing back 2/10 Key Learnings from Y Combinator for Founders Harry inquires about learnings from Y Combinator and when a founder should accept a lower valuation. Jon explains why quibbling over seed valuations is shortsighted compared to choosing aligned long-term board partners.15:06–17:08 · Harry pushing back 5/10 Building Long-Term Relationships vs. Transactional Fundraising Harry strongly challenges the trend of compressed two-week fundraising sprints, calling it crazy to select ten-year board members in days. Jon wholeheartedly agrees, elaborating on how continuous relationship building beats transactional fundraising.17:10–21:23 · Harry pushing back 0/10 Founder Mental Health, Self-Care, and Daily Gratitude Harry asks why founders neglect mental health, prompting Jon to share insights from his father, a psychiatrist, while calling out Silicon Valley hustle porn. Harry playfully accepts Jon's advice on therapy, exercise, and gratitude journaling.21:24–24:07 · Harry pushing back 0/10 Perspective, Humility, and the Advantages of Seasoned Founders Harry asks about the advantages of seasoned founders. Jon outlines how family life provides a daily mental reset and how mid-thirties maturity fosters humility and reduces ego-driven decision making.24:07–27:24 · Harry pushing back 1/10 Quickfire Round and Future Vision for Star City Harry runs through a quickfire round covering books, tech industry changes, and investor relationships. Jon challenges conventional fundraising advice and articulates Star City's vision to make major cities accessible.

speaking balance: gold is Harry, purple is the guest (3 minute bins)

0:00 · Harry 100% · guest 0%0:00 · Harry 100% · guest 0%3:00 · Harry 49.4% · guest 50.6%3:00 · Harry 49.4% · guest 50.6%6:00 · Harry 26.9% · guest 73.1%6:00 · Harry 26.9% · guest 73.1%9:00 · Harry 10.5% · guest 89.5%9:00 · Harry 10.5% · guest 89.5%12:00 · Harry 15.6% · guest 84.4%12:00 · Harry 15.6% · guest 84.4%15:00 · Harry 28.1% · guest 71.9%15:00 · Harry 28.1% · guest 71.9%18:00 · Harry 11.6% · guest 88.4%18:00 · Harry 11.6% · guest 88.4%21:00 · Harry 10.7% · guest 89.3%21:00 · Harry 10.7% · guest 89.3%24:00 · Harry 23% · guest 77%24:00 · Harry 23% · guest 77%27:00 · Harry 82.9% · guest 17.1%27:00 · Harry 82.9% · guest 17.1%30:00 · Harry 100% · guest 0%30:00 · Harry 100% · guest 0%
Sharpest disagreement ▶ 25:38 Rejecting conventional fundraising mode advice

Jon explicitly pushes back against standard Silicon Valley wisdom that founders must strictly alternate between fundraising mode and non-fundraising mode, calling it transactional and flawed.

 Hardest push from Harry ▶ 14:54 Challenging two-week fundraising sprints

Harry explicitly refuses the popular framing that compressed two-week fundraising sprints are efficient, calling it crazy to pick a decade-long board member based on a three-day interaction.

 Biggest teaching moment ▶ 13:05 Reframing seed valuations vs board alignment

Jon educates Harry and the audience on why optimizing between seed valuation caps is silly compared to ensuring long-term partner alignment.

 Harry holds his own ▶ 8:41 Demonstrating VC pushback on asset-heavy models

Harry demonstrates his VC acumen by directly challenging Jon on the traditional VC skepticism around asset-heavy proptech startups.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Jon Dishotsky's Background and Founding of Star City 1100 Harry opens with a warm, supportive introduction asking about Jon's background and the origin story of Star City. Jon responds warmly, praising Harry's hustle and sharing his personal background growing up around multi-generational housing in Palo Alto.
PropTech Evolution and Asset-Heavy VC Fundraising 5325 Harry takes on a contrarian VC perspective, challenging Jon on why an investor shouldn't immediately dismiss Star City as an undesirable asset-heavy business model. Jon defends the model by walking through their customer research, MVP validation, and encouragement from Y Combinator.
Key Learnings from Y Combinator for Founders 3312 Harry inquires about learnings from Y Combinator and when a founder should accept a lower valuation. Jon explains why quibbling over seed valuations is shortsighted compared to choosing aligned long-term board partners.
Building Long-Term Relationships vs. Transactional Fundraising 5115 Harry strongly challenges the trend of compressed two-week fundraising sprints, calling it crazy to select ten-year board members in days. Jon wholeheartedly agrees, elaborating on how continuous relationship building beats transactional fundraising.
Founder Mental Health, Self-Care, and Daily Gratitude 1410 Harry asks why founders neglect mental health, prompting Jon to share insights from his father, a psychiatrist, while calling out Silicon Valley hustle porn. Harry playfully accepts Jon's advice on therapy, exercise, and gratitude journaling.
Perspective, Humility, and the Advantages of Seasoned Founders 2200 Harry asks about the advantages of seasoned founders. Jon outlines how family life provides a daily mental reset and how mid-thirties maturity fosters humility and reduces ego-driven decision making.
Quickfire Round and Future Vision for Star City 2221 Harry runs through a quickfire round covering books, tech industry changes, and investor relationships. Jon challenges conventional fundraising advice and articulates Star City's vision to make major cities accessible.

Statements from this episode (9)

Opinion
Dishotsky: WeWork set the stage for modern PropTech
“And I think WeWork was the first one that really sort of set the stage. Before that, there was really only like LoopNet and Zillow and Renfin. And, you know, those were really taking a very, you know, web two point O approach to prop tech of, Just being sort o…”
Jon Dishotsky May 17, 2019 ▶ 7:35
Disclosure
Dishotsky: Star City interviewed 750 prospective residents before launching
“We started the company by talking to 750 people who were making 50 to 120,000 dollars a year, who had full-time jobs, and were living in cities 20 to 50 years old.”
Jon Dishotsky May 17, 2019 ▶ 9:17
Insight
Dishotsky: Averaging advice from mentors leads to mediocre startup decisions
“Really try to not optimize on the average of all that advice, but really take in sort of the good and the bad, but take it and do it your way. And I think that's really, really important. Otherwise you'll end up with some of a lot of mediocre advice.”
Jon Dishotsky May 17, 2019 ▶ 12:29
Insight
Dishotsky: Optimizing seed valuation caps between $6M and $12M is pointless
“If you're trying to value invest at the seed stage, it's kind of a silly exercise. So I think that like optimizing between a six cap and a 12 cap is really like, I just don't know that that's going to be the right way to invest. I think you're just kind of lik…”
Jon Dishotsky May 17, 2019 ▶ 13:08
Disclosure
Starcity took a lower valuation offer from Bullpen Capital over bigger VCs
“We took on the folks from Eric Weizen from Bullpen Capital, and I'm just a huge fan of Bullpen Capital and what Paul has built over there. Their offer was a little bit lower, and they were sort of very transparent”
Jon Dishotsky May 17, 2019 ▶ 14:22
Opinion
Harry Stebbings: Selecting board members via rapid fundraising sprints is crazy
“So you're going to choose someone who you've met three days ago, who's given you a high valuation on a term sheet, and they're going to join your board and work with you for 10 years, and you're going to do that for efficiency's sake. That seems quite crazy to…”
Harry Stebbings May 17, 2019 ▶ 15:11
Insight
Jon Dishotsky: Founders should continuously build investor relationships instead of isolated sprints
“Without sort of soft pitching people throughout a series of meetings and You know, you really don't get a chance to build that relationship and your chances of success are just so much lower. Whereas I think you should just always be building fundraising relat…”
Jon Dishotsky May 17, 2019 ▶ 16:26
Opinion
Dishotsky: Initialized Capital deserves credit for calling out startup hustle porn culture
“And I actually have to give kudos to the initialized guys for taking down the notion of sort of hustle porn, as I would say. There's this concept in the valley that like you should just grind to the limits of your existence and think about yourself secondarily…”
Jon Dishotsky May 17, 2019 ▶ 17:55
Assertion Supported
Dishotsky: Seasoned founders statistically outperform younger founders
“And I actually think that the statistics are in our favor. The seasoned guys and gals are actually better performers in many cases, so.”
Jon Dishotsky May 17, 2019 ▶ 23:41
Made with StarZero

Turn any episode into a week of clips.

This entire site, over 1,200 episodes transcribed, diarized, checked and made playable, runs on the StarZero media pipeline. Drop in your own episode and the podcast clipper finds the moments worth sharing, cuts them, captions them, and reframes them for every feed.

Try the podcast clipper Learn more