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Jul 13, 2018 · 35m · 20vc

20VC: Why Fundraising Is Like Dating and How to Play The Game Successfully & How To Increase The Flexibility of Your Burn When Growth is Ambiguous with Rachel Blumenthal, Founder & CEO @ Rockets of Awesome

Rachel Blumenthal · 24m spoken Harry Stebbings · 9m 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, host Harry Stebbings interviews Rachel Blumenthal, founder and CEO of Rockets of Awesome, to discuss strategic fundraising techniques, capital efficiency, operator versus VC dynamics, and overcoming gender bias in the venture capital ecosystem.

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 27.7% of the talking time here. How this is scored →

Harry as informed peer 1.6 Guest teaching 4.4 Guest disagreement 1.8 Harry pushing back 1.6
05100:0010:0020:0030:003:01–8:37 · Harry as informed peer 0/10 Rachel Blumenthal's Career Journey & The Birth of Rockets of Awesome This introductory segment consists of a broad opening question followed by a detailed monologue from Rachel about her career from fashion jewelry to Cricket Circle and Rockets of Awesome. Because the host simply yields the floor for her background narrative, host expertise and pushback are zero.8:37–16:32 · Harry as informed peer 2/10 Fundraising as Dating & Managing Runway and Capital Harry asks targeted follow-up questions about how to operationalize scarcity in fundraising and manage burn rate. Rachel educates the host on playing the dating game in fundraising and balancing overhead flexibility.16:32–22:14 · Harry as informed peer 3/10 Operator Investors vs. Traditional VCs When Rachel criticizes traditional non-operator VCs for using jargon and shallow pattern recognition, Harry pushes back by putting himself in that group and asking for actionable advice. Rachel responds with a masterclass on how non-operators can build genuine category empathy.22:14–29:42 · Harry as informed peer 2/10 The New York Ecosystem & Navigating Bias as a Female Founder Rachel details systemic sexism in VC pitches, describing how she directly challenges investors who ask biased questions about balancing motherhood. While friendly toward Harry, her recounted stories show strong combativeness against industry bias.29:42–33:21 · Harry as informed peer 1/10 Quickfire Round & Future Vision for Rockets of Awesome In the quickfire round, Rachel humorously rejects the traditional book recommendation prompt by pointing out that running a business and parenting leaves no time for books. The dynamic remains lighthearted and rapid.3:01–8:37 · Guest teaching 3/10 Rachel Blumenthal's Career Journey & The Birth of Rockets of Awesome This introductory segment consists of a broad opening question followed by a detailed monologue from Rachel about her career from fashion jewelry to Cricket Circle and Rockets of Awesome. Because the host simply yields the floor for her background narrative, host expertise and pushback are zero.8:37–16:32 · Guest teaching 4/10 Fundraising as Dating & Managing Runway and Capital Harry asks targeted follow-up questions about how to operationalize scarcity in fundraising and manage burn rate. Rachel educates the host on playing the dating game in fundraising and balancing overhead flexibility.16:32–22:14 · Guest teaching 6/10 Operator Investors vs. Traditional VCs When Rachel criticizes traditional non-operator VCs for using jargon and shallow pattern recognition, Harry pushes back by putting himself in that group and asking for actionable advice. Rachel responds with a masterclass on how non-operators can build genuine category empathy.22:14–29:42 · Guest teaching 6/10 The New York Ecosystem & Navigating Bias as a Female Founder Rachel details systemic sexism in VC pitches, describing how she directly challenges investors who ask biased questions about balancing motherhood. While friendly toward Harry, her recounted stories show strong combativeness against industry bias.29:42–33:21 · Guest teaching 3/10 Quickfire Round & Future Vision for Rockets of Awesome In the quickfire round, Rachel humorously rejects the traditional book recommendation prompt by pointing out that running a business and parenting leaves no time for books. The dynamic remains lighthearted and rapid.3:01–8:37 · Guest disagreement 0/10 Rachel Blumenthal's Career Journey & The Birth of Rockets of Awesome This introductory segment consists of a broad opening question followed by a detailed monologue from Rachel about her career from fashion jewelry to Cricket Circle and Rockets of Awesome. Because the host simply yields the floor for her background narrative, host expertise and pushback are zero.8:37–16:32 · Guest disagreement 1/10 Fundraising as Dating & Managing Runway and Capital Harry asks targeted follow-up questions about how to operationalize scarcity in fundraising and manage burn rate. Rachel educates the host on playing the dating game in fundraising and balancing overhead flexibility.16:32–22:14 · Guest disagreement 2/10 Operator Investors vs. Traditional VCs When Rachel criticizes traditional non-operator VCs for using jargon and shallow pattern recognition, Harry pushes back by putting himself in that group and asking for actionable advice. Rachel responds with a masterclass on how non-operators can build genuine category empathy.22:14–29:42 · Guest disagreement 4/10 The New York Ecosystem & Navigating Bias as a Female Founder Rachel details systemic sexism in VC pitches, describing how she directly challenges investors who ask biased questions about balancing motherhood. While friendly toward Harry, her recounted stories show strong combativeness against industry bias.29:42–33:21 · Guest disagreement 2/10 Quickfire Round & Future Vision for Rockets of Awesome In the quickfire round, Rachel humorously rejects the traditional book recommendation prompt by pointing out that running a business and parenting leaves no time for books. The dynamic remains lighthearted and rapid.3:01–8:37 · Harry pushing back 0/10 Rachel Blumenthal's Career Journey & The Birth of Rockets of Awesome This introductory segment consists of a broad opening question followed by a detailed monologue from Rachel about her career from fashion jewelry to Cricket Circle and Rockets of Awesome. Because the host simply yields the floor for her background narrative, host expertise and pushback are zero.8:37–16:32 · Harry pushing back 2/10 Fundraising as Dating & Managing Runway and Capital Harry asks targeted follow-up questions about how to operationalize scarcity in fundraising and manage burn rate. Rachel educates the host on playing the dating game in fundraising and balancing overhead flexibility.16:32–22:14 · Harry pushing back 3/10 Operator Investors vs. Traditional VCs When Rachel criticizes traditional non-operator VCs for using jargon and shallow pattern recognition, Harry pushes back by putting himself in that group and asking for actionable advice. Rachel responds with a masterclass on how non-operators can build genuine category empathy.22:14–29:42 · Harry pushing back 2/10 The New York Ecosystem & Navigating Bias as a Female Founder Rachel details systemic sexism in VC pitches, describing how she directly challenges investors who ask biased questions about balancing motherhood. While friendly toward Harry, her recounted stories show strong combativeness against industry bias.29:42–33:21 · Harry pushing back 1/10 Quickfire Round & Future Vision for Rockets of Awesome In the quickfire round, Rachel humorously rejects the traditional book recommendation prompt by pointing out that running a business and parenting leaves no time for books. The dynamic remains lighthearted and rapid.

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 12.7% · guest 87.3%3:00 · Harry 12.7% · guest 87.3%6:00 · Harry 12.2% · guest 87.8%6:00 · Harry 12.2% · guest 87.8%9:00 · Harry 27.9% · guest 72.1%9:00 · Harry 27.9% · guest 72.1%12:00 · Harry 9.8% · guest 90.2%12:00 · Harry 9.8% · guest 90.2%15:00 · Harry 11.5% · guest 88.5%15:00 · Harry 11.5% · guest 88.5%18:00 · Harry 7.6% · guest 92.4%18:00 · Harry 7.6% · guest 92.4%21:00 · Harry 23.5% · guest 76.5%21:00 · Harry 23.5% · guest 76.5%24:00 · Harry 1.3% · guest 98.7%24:00 · Harry 1.3% · guest 98.7%27:00 · Harry 27.9% · guest 72.1%27:00 · Harry 27.9% · guest 72.1%30:00 · Harry 15% · guest 85%30:00 · Harry 15% · guest 85%33:00 · Harry 92.2% · guest 7.8%33:00 · Harry 92.2% · guest 7.8%
Sharpest disagreement ▶ 24:30 Confronting sexist investor questions

Rachel recounts shutting down biased male VCs asking how she manages work-life balance by looking them in the eye and replying 'exactly the way my husband does.'

 Hardest push from Harry ▶ 18:29 Harry identifies as a non-operator VC and asks for constructive critique

Harry refuses to let Rachel's dismissal of non-operator VCs pass without challenging her to explain how non-operators like himself can deliver real value.

 Biggest teaching moment ▶ 18:43 Explaining the limitations of VC pattern recognition

Rachel breaks down why traditional VCs rely on superficial industry jargon and broad generalizations, giving the host concrete guidance on deep category immersion.

 Harry holds his own ▶ 22:14 Harry articulates the lack of conviction in the NY investor ecosystem

Harry demonstrates ecosystem expertise by pointing out how New York VC funding is often shallower in conviction lead investors than media perception suggests.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Rachel Blumenthal's Career Journey & The Birth of Rockets of Awesome 0300 This introductory segment consists of a broad opening question followed by a detailed monologue from Rachel about her career from fashion jewelry to Cricket Circle and Rockets of Awesome. Because the host simply yields the floor for her background narrative, host expertise and pushback are zero.
Fundraising as Dating & Managing Runway and Capital 2412 Harry asks targeted follow-up questions about how to operationalize scarcity in fundraising and manage burn rate. Rachel educates the host on playing the dating game in fundraising and balancing overhead flexibility.
Operator Investors vs. Traditional VCs 3623 When Rachel criticizes traditional non-operator VCs for using jargon and shallow pattern recognition, Harry pushes back by putting himself in that group and asking for actionable advice. Rachel responds with a masterclass on how non-operators can build genuine category empathy.
The New York Ecosystem & Navigating Bias as a Female Founder 2642 Rachel details systemic sexism in VC pitches, describing how she directly challenges investors who ask biased questions about balancing motherhood. While friendly toward Harry, her recounted stories show strong combativeness against industry bias.
Quickfire Round & Future Vision for Rockets of Awesome 1321 In the quickfire round, Rachel humorously rejects the traditional book recommendation prompt by pointing out that running a business and parenting leaves no time for books. The dynamic remains lighthearted and rapid.

Statements from this episode (10)

Insight
Blumenthal: Kids' apparel is a larger recurring opportunity than strollers
“What becomes the pain point is that your kids are growing so rapidly, and every two to three months at that period of time, they're outgrowing their clothes, and keeping that dresser stocked with clothes that fit your kids that don't become crop tops and cropp…”
Rachel Blumenthal Jul 13, 2018 ▶ 7:46
Insight
Blumenthal: Founders must create scarcity and play hard-to-get with VCs
“Nobody, whether it's an investment, or it's a cookie as it relates to kids, or it's a car when you go and buy your car, nobody wants something that they can easily get, right? Everybody wants a challenge, and so when fundraising, it's really important to play …”
Rachel Blumenthal Jul 13, 2018 ▶ 9:34
Insight
Blumenthal: Former operators make better VCs due to empathy and prioritization
“An investor that was an operator, which I have to say is really hard to find, but an investor that was an operator, I'd say first and foremost, really understands how hard it is to be a founder, how hard it is to be an operating team, and so there's a sensitiv…”
Rachel Blumenthal Jul 13, 2018 ▶ 16:43
Opinion
Blumenthal: Kirsten Green is a standout investor despite lacking operator background
“Where I have had the greatest success is is in one of my longest time investors being Kirsten Green from Forerunner in that Kirsten loves consumers. She loves retail. She intimately understands the consumer and understands the dynamic between consumers and dif…”
Rachel Blumenthal Jul 13, 2018 ▶ 20:50
Opinion
Blumenthal: Venture investors lack conviction and display follower mentality
“I often find that there's generally not much conviction across the board and that there's a lot of follower type behavior where everybody wants to get in on a deal, a business, an opportunity that everybody else wants to be in on. It creates this follower ment…”
Rachel Blumenthal Jul 13, 2018 ▶ 22:17
Assertion Supported
Investors ask male founders about opportunity and female founders about risk
“There's statistically significant data in research that will tell you that when male founders are meeting with investors, whether they're male or female investors, they are asked the question of what is the greatest opportunity that you have ahead of you? And …”
Rachel Blumenthal Jul 13, 2018 ▶ 23:16
Insight
Blumenthal: Successful leaders project confidence and fake it through imposter syndrome
“The reality is that we all have imposter syndrome, right? We all think that we're not good enough or we're not there yet, but the ones that succeed are the ones that fake it. We just fake it every single day and we put on the air of confidence, whether we're C…”
Rachel Blumenthal Jul 13, 2018 ▶ 27:36
Insight
Blumenthal: Certain categories will never innovate without female founders and investors
“There are categories that will never be innovative if we don't have female entrepreneurs and female investors, right?”
Rachel Blumenthal Jul 13, 2018 ▶ 28:35
Prediction Didn’t hold up
Blumenthal: Rockets of Awesome will dominate children's apparel in five years
“We're going to dominate children's apparel. We are going to be the number one place that both parents and kids want to shop”
Rachel Blumenthal Jul 13, 2018 ▶ 32:33
Opinion
Blumenthal: Incumbent apparel retailers neglect dual kids-and-parents customer dynamic
“That has very much been forgotten in any of the incumbents, and it's critical in the success of this category that we understand the demands and the needs and the psychology of both of those constituents”
Rachel Blumenthal Jul 13, 2018 ▶ 32:51
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