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Oct 29, 2020 · 19m · how-i-built-this

How I Built Resilience: Cheryl Contee of Do Big Things

Cheryl Contee · 12m spoken Guy Raz · 5m spoken
0:00 / 0:00

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In this episode of How I Built This: Resilience Edition, host Guy Raz interviews entrepreneur Cheryl Contee about navigating systemic bias, overcoming imposter syndrome, and building mission-driven digital ventures as an underrepresented founder.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Guy holds 33.1% of the talking time here. How this is scored →

Guy as informed peer 2.8 Guest teaching 2.6 Guest disagreement 0.8 Guy pushing back 0.0
05100:0010:000:37–4:28 · Guy as informed peer 3/10 Introducing Cheryl Contee and the Mission of Do Big Things Guy introduces Cheryl Contee and outlines her resume, demonstrating solid background research on Attentive.ly and Do Big Things. Cheryl explains how her digital agency helps mission-driven causes and shares the barriers she overcame as a Black female founder.4:28–7:26 · Guy as informed peer 4/10 Breaking Entrepreneurial Stereotypes and Pitching to Investors Guy references Contee's Harvard Business Review article regarding startup fundraising for non-white founders. Contee uses the vivid metaphor of a mechanical bull to explain systemic double standards and stresses using data to win over skeptical venture capitalists.7:27–11:41 · Guy as informed peer 2/10 Mid-Show Teaser and Book Promotion Break After a brief mid-show book promo, Guy asks Cheryl about overcoming imposter syndrome. Cheryl shares personal experiences of being the only Black woman in tech rooms and details how intentional networking built her career.11:42–14:40 · Guy as informed peer 1/10 Audience Q&A: Authentic Inclusion and Minority Recruitment Guy acts as a facilitator, reading listener questions from Twitter and LinkedIn about systemic racism in marketing and minority talent recruitment. Cheryl explains practical, proactive steps companies must take to step outside their comfort zones.14:40–18:49 · Guy as informed peer 4/10 Audience Q&A: Startup Capital and Geographic Equity Guy draws on previous interviews with venture capitalists to probe how founders outside primary coastal hubs can access capital. Cheryl educates the audience on geographic equity, leveraging pandemic-era remote dynamics, and remaining assertive in investor outreach.0:37–4:28 · Guest teaching 2/10 Introducing Cheryl Contee and the Mission of Do Big Things Guy introduces Cheryl Contee and outlines her resume, demonstrating solid background research on Attentive.ly and Do Big Things. Cheryl explains how her digital agency helps mission-driven causes and shares the barriers she overcame as a Black female founder.4:28–7:26 · Guest teaching 3/10 Breaking Entrepreneurial Stereotypes and Pitching to Investors Guy references Contee's Harvard Business Review article regarding startup fundraising for non-white founders. Contee uses the vivid metaphor of a mechanical bull to explain systemic double standards and stresses using data to win over skeptical venture capitalists.7:27–11:41 · Guest teaching 2/10 Mid-Show Teaser and Book Promotion Break After a brief mid-show book promo, Guy asks Cheryl about overcoming imposter syndrome. Cheryl shares personal experiences of being the only Black woman in tech rooms and details how intentional networking built her career.11:42–14:40 · Guest teaching 3/10 Audience Q&A: Authentic Inclusion and Minority Recruitment Guy acts as a facilitator, reading listener questions from Twitter and LinkedIn about systemic racism in marketing and minority talent recruitment. Cheryl explains practical, proactive steps companies must take to step outside their comfort zones.14:40–18:49 · Guest teaching 3/10 Audience Q&A: Startup Capital and Geographic Equity Guy draws on previous interviews with venture capitalists to probe how founders outside primary coastal hubs can access capital. Cheryl educates the audience on geographic equity, leveraging pandemic-era remote dynamics, and remaining assertive in investor outreach.0:37–4:28 · Guest disagreement 1/10 Introducing Cheryl Contee and the Mission of Do Big Things Guy introduces Cheryl Contee and outlines her resume, demonstrating solid background research on Attentive.ly and Do Big Things. Cheryl explains how her digital agency helps mission-driven causes and shares the barriers she overcame as a Black female founder.4:28–7:26 · Guest disagreement 1/10 Breaking Entrepreneurial Stereotypes and Pitching to Investors Guy references Contee's Harvard Business Review article regarding startup fundraising for non-white founders. Contee uses the vivid metaphor of a mechanical bull to explain systemic double standards and stresses using data to win over skeptical venture capitalists.7:27–11:41 · Guest disagreement 0/10 Mid-Show Teaser and Book Promotion Break After a brief mid-show book promo, Guy asks Cheryl about overcoming imposter syndrome. Cheryl shares personal experiences of being the only Black woman in tech rooms and details how intentional networking built her career.11:42–14:40 · Guest disagreement 1/10 Audience Q&A: Authentic Inclusion and Minority Recruitment Guy acts as a facilitator, reading listener questions from Twitter and LinkedIn about systemic racism in marketing and minority talent recruitment. Cheryl explains practical, proactive steps companies must take to step outside their comfort zones.14:40–18:49 · Guest disagreement 1/10 Audience Q&A: Startup Capital and Geographic Equity Guy draws on previous interviews with venture capitalists to probe how founders outside primary coastal hubs can access capital. Cheryl educates the audience on geographic equity, leveraging pandemic-era remote dynamics, and remaining assertive in investor outreach.0:37–4:28 · Guy pushing back 0/10 Introducing Cheryl Contee and the Mission of Do Big Things Guy introduces Cheryl Contee and outlines her resume, demonstrating solid background research on Attentive.ly and Do Big Things. Cheryl explains how her digital agency helps mission-driven causes and shares the barriers she overcame as a Black female founder.4:28–7:26 · Guy pushing back 0/10 Breaking Entrepreneurial Stereotypes and Pitching to Investors Guy references Contee's Harvard Business Review article regarding startup fundraising for non-white founders. Contee uses the vivid metaphor of a mechanical bull to explain systemic double standards and stresses using data to win over skeptical venture capitalists.7:27–11:41 · Guy pushing back 0/10 Mid-Show Teaser and Book Promotion Break After a brief mid-show book promo, Guy asks Cheryl about overcoming imposter syndrome. Cheryl shares personal experiences of being the only Black woman in tech rooms and details how intentional networking built her career.11:42–14:40 · Guy pushing back 0/10 Audience Q&A: Authentic Inclusion and Minority Recruitment Guy acts as a facilitator, reading listener questions from Twitter and LinkedIn about systemic racism in marketing and minority talent recruitment. Cheryl explains practical, proactive steps companies must take to step outside their comfort zones.14:40–18:49 · Guy pushing back 0/10 Audience Q&A: Startup Capital and Geographic Equity Guy draws on previous interviews with venture capitalists to probe how founders outside primary coastal hubs can access capital. Cheryl educates the audience on geographic equity, leveraging pandemic-era remote dynamics, and remaining assertive in investor outreach.

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

0:00 · Guy 58.5% · guest 41.5%0:00 · Guy 58.5% · guest 41.5%3:00 · Guy 6.4% · guest 93.6%3:00 · Guy 6.4% · guest 93.6%6:00 · Guy 71.8% · guest 28.2%6:00 · Guy 71.8% · guest 28.2%9:00 · Guy 26.7% · guest 73.3%9:00 · Guy 26.7% · guest 73.3%12:00 · Guy 10.5% · guest 89.5%12:00 · Guy 10.5% · guest 89.5%15:00 · Guy 16% · guest 84%15:00 · Guy 16% · guest 84%18:00 · Guy 49.8% · guest 50.2%18:00 · Guy 49.8% · guest 50.2%
Sharpest disagreement ▶ 5:31 Critique of Venture Double Standards

Cheryl forcefully dismantles the traditional startup stereotype, contrasting how male and female founders are judged on a mechanical bull and describing her journey as dancing backwards in heels.

 Hardest push from Guy ▶ 16:09 Challenging Geographic Fundraising Access

Guy presses on the practical limitations of fundraising for Black entrepreneurs located outside traditional venture ecosystems like New York or Silicon Valley.

 Biggest teaching moment ▶ 6:46 Educating on Pitching Unfamiliar Markets to VCs

Cheryl articulates how founders of color must educate traditional white male investors by translating community-focused solutions into undeniable market data.

 Guy holds their own ▶ 6:10 Synthesizing HBR Insights

Guy shows strong command of Cheryl's published thought leadership, citing specific takeaways from her Harvard Business Review piece on venture funding dynamics.
the scores for every segment, with the reasoning behind each
ChapterTopicGuy as informed peerGuest teachingGuest disagreementGuy pushing backWhy
Introducing Cheryl Contee and the Mission of Do Big Things 3210 Guy introduces Cheryl Contee and outlines her resume, demonstrating solid background research on Attentive.ly and Do Big Things. Cheryl explains how her digital agency helps mission-driven causes and shares the barriers she overcame as a Black female founder.
Breaking Entrepreneurial Stereotypes and Pitching to Investors 4310 Guy references Contee's Harvard Business Review article regarding startup fundraising for non-white founders. Contee uses the vivid metaphor of a mechanical bull to explain systemic double standards and stresses using data to win over skeptical venture capitalists.
Mid-Show Teaser and Book Promotion Break 2200 After a brief mid-show book promo, Guy asks Cheryl about overcoming imposter syndrome. Cheryl shares personal experiences of being the only Black woman in tech rooms and details how intentional networking built her career.
Audience Q&A: Authentic Inclusion and Minority Recruitment 1310 Guy acts as a facilitator, reading listener questions from Twitter and LinkedIn about systemic racism in marketing and minority talent recruitment. Cheryl explains practical, proactive steps companies must take to step outside their comfort zones.
Audience Q&A: Startup Capital and Geographic Equity 4310 Guy draws on previous interviews with venture capitalists to probe how founders outside primary coastal hubs can access capital. Cheryl educates the audience on geographic equity, leveraging pandemic-era remote dynamics, and remaining assertive in investor outreach.

Statements from this episode (6)

Disclosure
Contee: Do Big Things likely to work on vaccine misinformation campaign
“We're likely to start working on a campaign targeted at misinformation around vaccines.”
Cheryl Contee Oct 29, 2020 ▶ 1:41
Assertion Not checkable as stated
Contee faced VC discrimination despite running another multi-million dollar agency
“As an all female team with a black female co-founder, it wasn't easy. To get funding. We had to work really hard, and I experienced, you know, some real discrimination despite, you know, running at the same time, you know, another digital agency that had pulle…”
Cheryl Contee Oct 29, 2020 ▶ 3:38
Insight
Contee: Diverse founders pitching white male investors must rely heavily on data
“At least what worked for me was data, data, data, data, right, and showing, look, you might not get this totally, this isn't a problem that I'm solving for you, wealthy, white, male investor, but there's a lot of people for whom this is an issue, and here's ho…”
Cheryl Contee Oct 29, 2020 ▶ 6:47
Opinion
Contee: The tech sector is generally welcoming of strong technical talent
“But I personally have found the tech sector to overall be relatively welcoming, especially if you have, you know, really strong technical skills, which are needed right now.”
Cheryl Contee Oct 29, 2020 ▶ 10:17
Assertion Not checkable as stated
Contee: Almost every fund I know is leaning into funding POC founders
“Almost every fund that I know is really looking at, you know, how can we lean in on funding people of color?”
Cheryl Contee Oct 29, 2020 ▶ 15:21
Prediction Not checkable as stated
Contee: Startups led by women, minorities, and rural founders are undervalued
“Doubling down on investing in small businesses, especially from women, especially from minorities, especially from rural areas in innovative startups that are rising up because those are the businesses right now that are undervalued and are going to overperfor…”
Cheryl Contee Oct 29, 2020 ▶ 18:32
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