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Mar 10, 2016 · 17m · top-founders

Growing to $50k/mo with Roost CEO Jon Gillon Ep 202

John Gillen · 9m spoken Nathan Latka · 5m 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 Top, host Nathan Latka interviews Roost CEO Jon Gillon to discuss how his peer-to-peer storage marketplace achieved $50,000 in monthly revenue, overcame early startup failures, and structured an $8 million seed round.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 37.8% of the talking time here. How this is scored →

Nathan as informed peer 2.8 Guest teaching 1.6 Guest disagreement 1.0 Nathan pushing back 1.6
05100:0010:001:07–4:54 · Nathan as informed peer 3/10 Jon Gillon on Early Ventures and Lessons from Failure Nathan probes into Jon's background and four failed startups, asking how much money was lost. Jon explains the lessons learned around managing expectations when hiring technical talent.4:54–7:34 · Nathan as informed peer 4/10 Roost Marketplace Concept and Revenue Growth Nathan attempts to map Roost's competitive landscape with names like Breather and Sparefoot. Jon corrects the categorizations, distinguishing valet storage and office rentals from peer-to-peer storage marketplaces.7:34–12:36 · Nathan as informed peer 4/10 Seed Funding Rounds, Team Expansion, and Finding a Co-Founder Nathan drills down on fundraising mechanics, convertible notes versus priced equity rounds, and valuation expectations. Jon openly details his $8-9M pre-money target and his TaskRabbit tactic for finding a co-founder.12:37–16:39 · Nathan as informed peer 3/10 Mid-Show Promotion and HostGator Sponsorship Segment includes an ad read followed by the Famous Five rapid-fire questions. Nathan demonstrates relevant knowledge by citing insights from Jack Dorsey's former boss regarding executive time-batching.16:39–17:23 · Nathan as informed peer 0/10 Episode Conclusion, Key Takeaways, and Next Episode Teaser Host closing monologue summarizing the episode valuation highlights and previewing the next episode.1:07–4:54 · Guest teaching 2/10 Jon Gillon on Early Ventures and Lessons from Failure Nathan probes into Jon's background and four failed startups, asking how much money was lost. Jon explains the lessons learned around managing expectations when hiring technical talent.4:54–7:34 · Guest teaching 3/10 Roost Marketplace Concept and Revenue Growth Nathan attempts to map Roost's competitive landscape with names like Breather and Sparefoot. Jon corrects the categorizations, distinguishing valet storage and office rentals from peer-to-peer storage marketplaces.7:34–12:36 · Guest teaching 2/10 Seed Funding Rounds, Team Expansion, and Finding a Co-Founder Nathan drills down on fundraising mechanics, convertible notes versus priced equity rounds, and valuation expectations. Jon openly details his $8-9M pre-money target and his TaskRabbit tactic for finding a co-founder.12:37–16:39 · Guest teaching 1/10 Mid-Show Promotion and HostGator Sponsorship Segment includes an ad read followed by the Famous Five rapid-fire questions. Nathan demonstrates relevant knowledge by citing insights from Jack Dorsey's former boss regarding executive time-batching.16:39–17:23 · Guest teaching 0/10 Episode Conclusion, Key Takeaways, and Next Episode Teaser Host closing monologue summarizing the episode valuation highlights and previewing the next episode.1:07–4:54 · Guest disagreement 1/10 Jon Gillon on Early Ventures and Lessons from Failure Nathan probes into Jon's background and four failed startups, asking how much money was lost. Jon explains the lessons learned around managing expectations when hiring technical talent.4:54–7:34 · Guest disagreement 2/10 Roost Marketplace Concept and Revenue Growth Nathan attempts to map Roost's competitive landscape with names like Breather and Sparefoot. Jon corrects the categorizations, distinguishing valet storage and office rentals from peer-to-peer storage marketplaces.7:34–12:36 · Guest disagreement 1/10 Seed Funding Rounds, Team Expansion, and Finding a Co-Founder Nathan drills down on fundraising mechanics, convertible notes versus priced equity rounds, and valuation expectations. Jon openly details his $8-9M pre-money target and his TaskRabbit tactic for finding a co-founder.12:37–16:39 · Guest disagreement 1/10 Mid-Show Promotion and HostGator Sponsorship Segment includes an ad read followed by the Famous Five rapid-fire questions. Nathan demonstrates relevant knowledge by citing insights from Jack Dorsey's former boss regarding executive time-batching.16:39–17:23 · Guest disagreement 0/10 Episode Conclusion, Key Takeaways, and Next Episode Teaser Host closing monologue summarizing the episode valuation highlights and previewing the next episode.1:07–4:54 · Nathan pushing back 2/10 Jon Gillon on Early Ventures and Lessons from Failure Nathan probes into Jon's background and four failed startups, asking how much money was lost. Jon explains the lessons learned around managing expectations when hiring technical talent.4:54–7:34 · Nathan pushing back 3/10 Roost Marketplace Concept and Revenue Growth Nathan attempts to map Roost's competitive landscape with names like Breather and Sparefoot. Jon corrects the categorizations, distinguishing valet storage and office rentals from peer-to-peer storage marketplaces.7:34–12:36 · Nathan pushing back 2/10 Seed Funding Rounds, Team Expansion, and Finding a Co-Founder Nathan drills down on fundraising mechanics, convertible notes versus priced equity rounds, and valuation expectations. Jon openly details his $8-9M pre-money target and his TaskRabbit tactic for finding a co-founder.12:37–16:39 · Nathan pushing back 1/10 Mid-Show Promotion and HostGator Sponsorship Segment includes an ad read followed by the Famous Five rapid-fire questions. Nathan demonstrates relevant knowledge by citing insights from Jack Dorsey's former boss regarding executive time-batching.16:39–17:23 · Nathan pushing back 0/10 Episode Conclusion, Key Takeaways, and Next Episode Teaser Host closing monologue summarizing the episode valuation highlights and previewing the next episode.

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

0:00 · Nathan 63.2% · guest 36.8%0:00 · Nathan 63.2% · guest 36.8%3:00 · Nathan 12.8% · guest 87.2%3:00 · Nathan 12.8% · guest 87.2%6:00 · Nathan 32.5% · guest 67.5%6:00 · Nathan 32.5% · guest 67.5%9:00 · Nathan 12.9% · guest 87.1%9:00 · Nathan 12.9% · guest 87.1%12:00 · Nathan 55.9% · guest 44.1%12:00 · Nathan 55.9% · guest 44.1%15:00 · Nathan 53.3% · guest 46.7%15:00 · Nathan 53.3% · guest 46.7%
Sharpest disagreement ▶ 5:21 Jon correcting Nathan's competitor comparisons

When Nathan suggests Breather and Sparefoot as direct competitors, Jon quickly pushes back to explain that Breather is for office space and Sparefoot is actually a partner.

 Hardest push from Nathan ▶ 8:02 Nathan challenging Jon on outright buyout valuation

Nathan directly presses whether Jon would accept an immediate buyout offer if someone offered his targeted $8-9M valuation today.

 Biggest teaching moment ▶ 5:21 Distinguishing peer-to-peer storage models

Jon educates Nathan on the difference between valet on-demand storage companies like Boxbee/MakeSpace and Roost's peer-to-peer marketplace model.

 Nathan holds their own ▶ 14:48 Nathan detailing Dorsey's operational scheduling

Nathan adds concrete domain knowledge when discussing Jack Dorsey by sharing insights directly learned from interviewing Dorsey's former manager about batching days across companies.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Jon Gillon on Early Ventures and Lessons from Failure 3212 Nathan probes into Jon's background and four failed startups, asking how much money was lost. Jon explains the lessons learned around managing expectations when hiring technical talent.
Roost Marketplace Concept and Revenue Growth 4323 Nathan attempts to map Roost's competitive landscape with names like Breather and Sparefoot. Jon corrects the categorizations, distinguishing valet storage and office rentals from peer-to-peer storage marketplaces.
Seed Funding Rounds, Team Expansion, and Finding a Co-Founder 4212 Nathan drills down on fundraising mechanics, convertible notes versus priced equity rounds, and valuation expectations. Jon openly details his $8-9M pre-money target and his TaskRabbit tactic for finding a co-founder.
Mid-Show Promotion and HostGator Sponsorship 3111 Segment includes an ad read followed by the Famous Five rapid-fire questions. Nathan demonstrates relevant knowledge by citing insights from Jack Dorsey's former boss regarding executive time-batching.
Episode Conclusion, Key Takeaways, and Next Episode Teaser 0000 Host closing monologue summarizing the episode valuation highlights and previewing the next episode.

Statements from this episode (9)

Disclosure
Gillon raised $35,000 total across all of his failed startup businesses
“For all the businesses about, it's probably about 35,000 dollars.”
John Gillen Mar 10, 2016 ▶ 4:12
Disclosure
Gillon funded a past startup via Airbnb rentals for early profitability
“Droperty tax, I actually funded via Airbnb. And I was renting out my place on Airbnb and funding the business, and we're profitable pretty quickly.”
John Gillen Mar 10, 2016 ▶ 4:27
Disclosure
Roost charges a 15% monthly transaction fee on storage and parking
“So we take a 15% transaction fee Per month in perpetuity on these big transactions.”
John Gillen Mar 10, 2016 ▶ 6:02
Assertion Not checkable as stated
Roost generated $50,000 in top-line revenue in December 2015
“December of 2015, we did 50,000 dollars.”
John Gillen Mar 10, 2016 ▶ 6:54
Assertion Not checkable as stated
Roost is growing monthly revenue at 35% to 40% month-over-month
“Yeah, we launched pretty quickly, and now we're growing about 35% a month, 40% a month actually.”
John Gillen Mar 10, 2016 ▶ 7:20
Disclosure
Roost raised $1.46M in notes before pursuing a $2M priced round
“So we did a 160,000 dollars convertible note, then we did a 300,000 dollar convertible note, and then we did a million dollar convertible note, and now we're doing a price round. I'm raising two million dollars right now on a price feed round.”
John Gillen Mar 10, 2016 ▶ 7:38
Prediction Didn’t hold up
Gillon predicts Roost's $2M seed round will price at $8M-$9M pre-money
“We, we're looking for a lead investor right now, but if I were to see the future, I'd say about eight or nine million.”
John Gillen Mar 10, 2016 ▶ 7:57
Assertion Supported
Zipcar and Enterprise are major commercial partners for Roost
“Looking at Zipcar and Enterprise, also who are big partners of ours.”
John Gillen Mar 10, 2016 ▶ 9:31
Assertion Not checkable as stated
Gillon found his technical co-founder via a $75 TaskRabbit introduction ad
“So what I did was I actually put out an ad on TaskRabbit, back when, you know, you could do anything on TaskRabbit, you didn't have to be a professional and I put out an ad on TaskRabbit saying, seeking introduction to a technical person with an entrepreneuria…”
John Gillen Mar 10, 2016 ▶ 10:21
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