Interviews with incredible people

I did 200+ interviews with founders, operators, and investors and here's what we can learn

Shishir Mehrotra, co-founder and CEO of Coda on leadership, prioritization, product launches, and creating impact

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I did 200+ interviews with founders, operators, and investors and here's what we can learn

Key takeaways from 200+ interviews

Jessica Li

I have published 200+ interviews. It has been an incredibly rewarding journey of getting to know, working with, and learning from so many incredible individuals working globally in a wide range of sectors from healthcare to fintech to real estate to venture capital to public markets to consumer and more.

At this milestone, I wanted to reflect back on every interview I have done starting from the very beginning in early 2019. While I have categorized these on my website (bit.ly/jessicali) by role (founder, operator, and investor) and industry, I felt it would be immensely more useful to categorize them by tactical insight, so people looking for guidance around a specific topic can immediately find the advice and inspiration here regardless of role or industry and be immediately “mentored” by others through accessible content.

So I have done just that: categorized all 200+ interviews (and will continue to do so) by strategic focus area, including finding your problem, building user focused products, scaling, building your network, learning about new spaces, learning technical skills, navigating discrimination, and much more.

I am excited to share this with you all and welcome any feedback, questions, or recommendations for other people to feature. DM me

@jessicafeiyali⁠

and check out more content at beacons.ai/jessicali

Founders

Fundraising

⁠

Lauren Nkuranga, founder of GET IT⁠

⁠

Roshawnna Novellus, founder of EnrichHER⁠

⁠

Susan Liu, investor at Scale Venture Partners⁠

⁠

David Brown, founder of Techstars⁠

⁠

Ishan Sinha, VP at Point72 Ventures⁠

⁠

Nitesh Banta, founder of B12 and Rough Draft Ventures⁠

⁠

Tyler Norwood, partner at Antler⁠

⁠

Rebecca Kaden, managing partner at Union Square Ventures⁠

⁠

Nisha Dua, founder of BBG Ventures⁠

⁠

Lucy Guo, founder of Scale AI and Backend Capital⁠

⁠

Sohila Zadran, serial entrepreneur in biotech⁠

⁠

Sydney Thomas, investor at Precursor⁠

⁠

Sarah Guo, GP at Greylock⁠

⁠

Anna Khan, GP at Charles River Ventures⁠

⁠

Joanne Chen, partner at Foundation Capital⁠

⁠

Pialy Aditya, chief strategy officer at Republic⁠

⁠

Iynna Halilou, global programs manager at Entrepreneurs Roundtable Accelerator⁠

⁠

Ha Nguyen, founding partner at Spero Ventures⁠

⁠

Alison Rosenthal, managing partner at Leadout Capital and lecturer at Stanford GSB⁠

⁠

Catharine Dockery, founding partner of Vice Ventures⁠

⁠

Mar Hershenson, founder of Pear VC⁠

⁠

Heather Hartnett, CEO and general partner of Human Ventures⁠

⁠

Courtney Lipkin, partner at Susa Ventures⁠

⁠

Jocelyn Kinsey, partner at DFJ Growth⁠

⁠

Ashley Ramirez, chief of staff and investor at Halogen Ventures⁠

⁠

Christina Jenkins, head of life sciences at Phoenix Venture Partners⁠

⁠

Shruti Gandhi, GP at Array Ventures⁠

⁠

Lauren Kolodny, founding partner at Acrew Capital⁠

⁠

Jessica Peltz-Zatulove, founding partner at Hannah Grey VC⁠

⁠

Megan Ananian, general partner at The Helm⁠

⁠

Product

Finding your problem

⁠

Evan Walden, founder of Monday.vc and Getro⁠

⁠

Ben Pleat, founder of Cobu⁠

⁠

Adam Klein, founder of Season Three⁠

⁠

Neal Ganu, founder of Trio⁠

⁠

Shawn Hathiramani, founder of Flockjay⁠

⁠

Ben Salander and Mike Cipolla, founders of Verstaan⁠

⁠

Harnek Gulati, founder of MakerFleet⁠

⁠

Wil Eyi, founder of ToolBox⁠

⁠

Jack Roswell and Alex Zhuk, founders of Cloud Agronomics⁠

⁠

Myriam Maguire, founder of Maguire Boutique⁠

⁠

Olivia Zank, founder of BeneFactors⁠

⁠

Xiaoyin Qu, founder of Run the World⁠

⁠

Christian Maynard-Phillip, founder of Good Investor and former Chief Compliance Officer at Square⁠

⁠

John Capodilupo, founder of WHOOP⁠

⁠

Christelle Rohaut, founder of Codi⁠

⁠

Doll Avant, founder of Aquagenuity⁠

⁠

Caroline Early, chief of staff at This is L⁠

⁠

Emmanuel Quevy, founder of ProbiusDx⁠

⁠

Jared Friedman, partner at Y Combinator⁠

⁠

Warren Hogarth, founder of Empower⁠

⁠

Designing a user focused product

⁠

Emily Kenison, founder of Straplets⁠

⁠

Kristin Chen, CEO of Top.gg⁠

⁠

Sarah Lidgus, chief experience officer at Tempest⁠

⁠

Laura Schaffer, head of growth product at Twilio⁠

⁠

Sydney Shea, product designer at Aptible⁠

⁠

Teresa Man, lead designer at Superhuman⁠

⁠

Jenny Arden, senior director of design at Lyft⁠

⁠

Sara Cullen, founder of GEM⁠

⁠

Amy Rosenthal, head of product at FreeWill⁠

⁠

Reid Moncada, founder of Fitted⁠

⁠

Co-founders of Canary⁠

⁠

Sarah Stites, founder of Wavelength⁠

⁠

LaToya Westbrooks, UX researcher at Facebook⁠

⁠

Katie Doran, technical PM at Facebook⁠

⁠

Katie Tomezsko, PM at Quibi⁠

⁠

Julie Kim, product designer at Workday⁠

⁠

Shishir Mehrotra, founder of Coda⁠

⁠

Owen Phillips, founder of BrainKey⁠

⁠

Anamita Guha, global product lead at IBM⁠

⁠

Shanea Leven, head of product management at Lob and former senior director at Docker⁠

⁠

Allen Yang, head of product management and business operations at Bubble⁠

⁠

Ketki Duvvuru, product lead at Superhuman⁠

⁠

Courtney Hemphill, partner and technical lead at Carbon Five⁠

⁠

Yuhki Yamashita, VP of product at Figma⁠

⁠

Gabrielle Ruiz-Funes, head of digital innovation lab at Home Chef⁠

⁠

Priya Cutts, director of PMO at Rally Health⁠

⁠

James Ruben, founder of Hellosaurus⁠

⁠

Suelin Chen, founder of Cake⁠

⁠

Ambika Nigam, head of product at Bloomberg Media and design lead at IDEO⁠

⁠

Yasmin Kothari, product lead at Asana⁠

⁠

Amelia Lin, founder of Saga⁠

⁠

Catherine Winfield, director of design at the Chan Zuckerberg Initiative⁠

⁠

Russ Heddleston, co-founder and former CEO of Docsend⁠

⁠

Genevieve Ryan, founder of Realworld⁠

⁠

Brand building

⁠

Lyndie Benson, founder of Bleusault⁠

⁠

Taran Ghatrora, founder of Blume⁠

⁠

Noura Liben, founder of OpenBeauty⁠

⁠

SB Masters, namer of PayPal, Affirm, Concur, and Ariba⁠

⁠

Linda Ellison, founder of kau Health⁠

⁠

Moment’s founders⁠

⁠

Ariel Wengroff, founder of arfa⁠

⁠

Helena Merk, founder of Glimpse⁠

⁠

Calanthia Mei, director of strategy at Fast⁠

⁠

Alexandra Zitarain, founder of Eight Sleep⁠

⁠

Helena Hambrecht, founder of Haus⁠

⁠

Stephanie CN, head of career counseling at Skillcrush⁠

⁠

Hannah Yang, chief growth officer at the New York Times⁠

⁠

Polina Pompliano, founder of The Profile⁠

⁠

Samita, SVP of strategy and business development at NBCUniversal⁠

⁠

Rachel Carlson, co-founder and CEO of Guild Education⁠

⁠

Scaling

⁠

Amy Snook, COO at Haus⁠

⁠

Courtney Flynn, founder of Supply Savvy⁠

⁠

Matt Polega, founder of Mark43⁠

⁠

Emily Ellis, senior operations market manager at Lyft⁠

⁠

Benjamin Friedman, COO/CFO with 20 years of experience⁠

⁠

Annie Tsai, COO of Interact⁠

⁠

Larissa Rocha, employee #1 at Brex⁠

⁠

Judith Erwin, CEO of Grasshopper Bank⁠

⁠

Fang Yuan, director of investment at Baidu Ventures⁠

⁠

Jenny Qian, early employee at Twitch⁠

⁠

Charlene Banard, global head of technical operations at Novartis⁠

⁠

Michal Geller, SVP of global eCommerce marketing and product at Pepsi⁠

⁠

Mike Shore, VP and GM of enterprise at Axon⁠

⁠

Fei Fei, VP of sales operations and strategy at Gartner⁠

⁠

Ann Bordetsky, partner at NEA and former COO at Rival⁠

⁠

Julie Bell, COO of Emergence Capital⁠

⁠

Jim Haughwout, VP of platform at Peloton⁠

⁠

Leigh Marie Braswell, first PM at Scale AI and investor at Founders Fund⁠

⁠

Ilyse Kaplan, President and COO at Feather⁠

⁠

Grace Gimson, former head of market launch operations at Deliveroo and chief of staff at company acquired by Facebook⁠

⁠

Team

Finding co-founders

⁠

Renata Black, founder of EBY⁠

⁠

Sarah Badahman, founder of HIPAAtrek⁠

⁠

Amy Wagner, founder of Altress⁠

⁠

Matthew Huang, founder of Camelot⁠

⁠

Nabiha Saklayen, founder of Cellino⁠

⁠

Jason Cui and Annie Hwang, founders of Jemi⁠

⁠

Michelle Zatlyn, founder of Cloudflare⁠

⁠

Michael Shieh, founder of Appaegis⁠

⁠

Building teams

⁠

Halle Tecco, founder of Natalist⁠

⁠

Selina Tobaccowala, founder of Evite and Gixo and former president of SurveyMonkey⁠

⁠

Gillian Morris, founder of Hitlist⁠

⁠

Riley Long, former head of talent at Joymode and DogVacay⁠

⁠

Chas Pulido, founder of Alix Ventures⁠

⁠

Jordan Taylor and Edith Cooper, founders of Medley⁠

⁠

Tameika Scott, founder of Employee Choice⁠

⁠

Phillipe Noel, founder of Fractal⁠

⁠

Taciana Pereira, chief scientific officer at Allevi⁠

⁠

Joanna Lee, founder and general partner at f7⁠

⁠

Rich Horgan, founder of Cure Rare Disease⁠

⁠

Yana Welinder, founder of Kraftful⁠

⁠

Nan Ransohoff, head of climate at Stripe⁠

⁠

Brian Corey, founder of Outpatient⁠

⁠

Anvisha Pai, founder of Dover⁠

⁠

Joseph Sanborn, SVP of strategy at EverQuote⁠

⁠

Athena Kan, CEO of Dreambound⁠

⁠

Leading companies

⁠

Andra Vaduva, founder of Hiboo⁠

⁠

Josh Isner, chief revenue officer at Axon⁠

⁠

Jon Hay, head of data at Boston Red Sox⁠

⁠

Shama Hyder, founder of Zen Media⁠

⁠

Larissa Rocha, employee #1 at Brex⁠

⁠

Neta Meidav, founder of Vault Platform⁠

⁠

Lex Rovner, founder of 64-x⁠

⁠

Henry Doriner, founder of Meetingbird⁠

⁠

Toni Schneider, investor at True Ventures and former CEO at Automattic⁠

⁠

Jack Altman, founder of Lattice⁠

⁠

Christina Cacioppo, founder of Vanta⁠

⁠

Shivani Berry, founder of Ascend⁠

⁠

Angela Grady, EVP and chief of staff at Okta⁠

⁠

Sarah Jones Simmer, chief operating officer at Bumble⁠

⁠

Ali Rohde, chief of staff at Sourceress⁠

⁠

Jane Alexander, chief of staff to the CEO at Carta⁠

⁠

Alana Karen, director of search platforms at Google⁠

⁠

Sharon Marcil, chief marketing officer at BCG⁠

⁠

Miriam Donaldson, head of people at Novartis⁠

⁠

Nora Staebler, SVP of global digital at PIMCO⁠

⁠

Faryl Ury, director of communications at Aurora⁠

⁠

Courtney Duffy, head of creator policy engagement at Patreon⁠

⁠

Sarah Bolin, director of business technology at YouTube⁠

⁠

Sales/Marketing

⁠

Sara Mauskopf, founder of Winnie⁠

⁠

Laura D’Asaro, founder of Chirps⁠

⁠

Carla Dunham, CMO at Foxtrot⁠

⁠

Sarah LaFleur, founder of M.M. LaFleur⁠

⁠

Will Foussier, founder of AceUp⁠

⁠

Kevin March, founder of Floating Point Group⁠

⁠

Gaurab Chakrabarti, founder of Solugen⁠

⁠

Danika Laszuk, GM at Betaworks⁠

⁠

Elisa Schreiber, marketing partner at Greylock⁠

⁠

Claire Diaz-Ortiz, early Twitter, partner at Magma Partners, best selling author⁠

⁠

Marco Mahrus, SVP of BD at Brex⁠

⁠

Amanda Goetz, former VP of marketing at The Knot⁠

⁠

David Lessing, COO of Ray Dalio’s family office and former CRO at Addepar⁠

⁠

Susan Johnson, CMO of Prudential Financial⁠

⁠

Chloe Stewart, VP of global sales at Eventbrite⁠

⁠

Lindsay Chastain, senior director of global growth marketing and partnerships at Ancestry⁠

⁠

David Dintenfass, CMO and head of experience design at Fidelity⁠

⁠

Amin Shaykho, founder of Kadama⁠

⁠

Scott Rubin, CMO at Lux Capital⁠

⁠

Said Francis, head of corporate strategy and development at Moderna⁠

⁠

Helen Min, head of marketing at AngelList and former head of marketing at Plaid and Quora⁠

⁠

Kim Chen, head of growth and marketing at Modern Fertility⁠

⁠

Alexa Hall, senior program manager at Google Cloud⁠

⁠

Colleen O’Brien, chief marketing officer at Microsoft’s venture fund⁠

⁠

Gina Gotthilf, former VP of marketing at Duolingo⁠

⁠

Jay Parekh, VP of business development at Chime⁠

⁠

Rebecca Stone, chief marketing officer at Cisco Meraki⁠

⁠

Mindy Rehse, senior director at Expedia⁠

⁠

Alexis Gay, HubSpot podcast host⁠

⁠

Justine Jordan, chief marketing officer at Wildbit⁠

⁠

Melanie Masarin, founder of GHIA and former head of marketing at Dig Inn and head of retail and offline experiences at Glossier⁠

⁠

Investors

Building your personal brand

⁠

Gesche Haas, founder of Trailblazer Ventures⁠

⁠

Harry Stebbings, founder of Twenty Minute VC⁠

⁠

Kat Garcia, investor at BCG Digital Ventures⁠

⁠

Camille Rickets, head of marketing at Notion⁠

⁠

Medha Agarwal, investor at Redpoint⁠

⁠

Chanele McFarlane, TEDx speaker and talent brand lead at Capital One⁠

⁠

Ashley Braiser, partner at Lightspeed Venture Partners⁠

⁠

Hannah Shtein, founder coach⁠

⁠

Alex Konrad, senior editor at Forbes⁠

⁠

Megan Starr, head of impact at the Carlyle Group⁠

⁠

Ali Kriegsman, founder of Bulletin⁠

⁠

Bailey Richardson, early Instagram employee and head of community at Substack⁠

⁠

Lolita Taub, co-founder of The Community Fund⁠

⁠

Theresa Helmer, executive director of integrated content strategy at Disney⁠

⁠

Nadia Masri, founder of Perksy⁠

⁠

Susanne Daniels, global head of original content at YouTube⁠

⁠

Building your network

⁠

Lolita Taub, chief of staff at Catalyte⁠

⁠

Kelly Fryer, COO at Techstars Barclays Accelerator⁠

⁠

Allison Allen, head of global product operations at Uber Money⁠

⁠

Sutian Dong, founder of the Global Women in VC Directory⁠

⁠

Nick Friedman, founder of Board⁠

⁠

Kate McAndrew, investor at Bolt and founder of Women in Hardware⁠

⁠

Domonique Fines, director of engagement at All Raise⁠

⁠

Allie Miller, Forbes AI Innovator of the year, US head of AI BD at Amazon⁠

⁠

Milan Koch and Jeffrey Evans, co-founders of Mantis with the Chainsmokers⁠

⁠

Lily Sassoon, partner at Green Meadow Ventures (FabFitFun VC arm)⁠

⁠

Domitilla Caputo, head of SAP.io Foundry⁠

⁠

Shiyan Koh and Elizabeth Yin, managing partner and cofounder of Hustle Fund⁠

⁠

Zuhairah Washington, global head of strategic partners at Expedia⁠

⁠

Jaye Goldstein, head of program at Petri⁠

⁠

Shin-pei Tsay, global head of cities and transportation policy at Uber⁠

⁠

Mallun Yen, founder and partner at Operator Collective and previously head of global intellectual property at Cisco⁠

⁠

Learning about new spaces

⁠

Claire Shorall, founder of Topknot⁠

⁠

Brianne Kimmel, founder of Work Life Ventures⁠

⁠

Charity Majors, founder and CTO at Honeycomb⁠

⁠

Raquel Wilson, founder of Future Narratives and former UN officer⁠

⁠

Elena Giralt, product marketing at Zcash⁠

⁠

Suzanne Ciani, pioneer of electronic music⁠

⁠

Nikhil Sinha, CEO of GSVlabs⁠

⁠

Marcus Brauchli, Pulitzer Prize winner⁠

⁠

Sol Chen, founder of Clara Health⁠

⁠

Lucas Asher, CEO of Tower Equity⁠

⁠

Merritt Moore, quantum physicist and professional ballerina⁠

⁠

Ada Yang, international strategy and corporate affairs at Pinduoduo⁠

⁠

Melissa McSherry, global head of data, security, and identity products at Visa⁠

⁠

Thomas Pologruto, chief data architect at Blackstone⁠

⁠

Ina Fried, chief technology correspondent at Axios⁠

⁠

Matthew Arnold, head of sustainable finance at JPMorgan Chase⁠

⁠

Sheila Warren, head of digital assets, blockchain, and data at the World Economic Forum⁠

⁠

Elizabeth Ruzzo, founder of adyn⁠

⁠

Teddy Seem, founder of Outsiders Fund⁠

⁠

Mark Blake, global head of strategy at S&P Global⁠

⁠

Bertrand Irissou, founder of Brainome⁠

⁠

Ryan Sandler, founder of Truework⁠

⁠

Schuyler Moore, Director of Science & Technology for the Defense Innovation Board at the Department of Defense⁠

⁠

Operators

Finding the right role

⁠

Christine Hong, founder of Auby⁠

⁠

Ashley Montgomery, product manager at Facebook⁠

⁠

Emily St. Denis, head of platform at Female Founders Fund⁠

⁠

Melanie Malott, senior talent acquisition partner at Emarsys⁠

⁠

Kailash Sundaram, investor at Detroit Venture Partners⁠

⁠

Nick Hotchkin, COO at Weight Watchers⁠

⁠

Kanjun Qiu, founder of Generally Intelligent and former chief of staff at Dropbo⁠

Getting the role

⁠

Jessica Li, investor at Soma Capital⁠

⁠

Dan Wu, legal engineer at Immuta⁠

⁠

Justine and Olivia Moore, investors at Charles River Ventures⁠

⁠

Keely and Katharine, marketing lead and head of product at Cape Privacy⁠

⁠

Yi Liu, head of insights and operations at Gusto⁠

⁠

Learning technical skills

⁠

Jessica Yung, AI resident at Google Brain⁠

⁠

Pujaa Rajan, deep learning engineer at Node⁠

⁠

Yinting Huang, software engineer at FreeWill⁠

⁠

Jyoti Puri, engineer at Shogun⁠

⁠

Austen Allred, founder of Lambda School⁠

⁠

Nelly Yusupova, founder of TechSpeak for Entrepreneurs⁠

⁠

Rema Aluko, senior director of engineering at Fandango⁠

⁠

Evan Johnson, director of analytics and insights at Steady⁠

⁠

Carolyn Conway, admissions team at Y Combinator⁠

⁠

Balwinder Kaur, founding engineer at AppDynamics⁠

⁠

Leading teams at large companies

⁠

Robert Pearl, former CEO of Kaiser Permanente⁠

⁠

Susan Standiford, former CTO of IKEA⁠

⁠

Padmini Pyapali, founding engineer at Uber Eats and Uber Freight⁠

⁠

Stasha Rosen, Zapier analytics manager⁠

⁠

Sara Rosso, director of marketing at WordPress.com⁠

⁠

Belinda Runkle, director of engineering at Google⁠

⁠

Jessie Duan, engineering manager at Quora⁠

⁠

Jordanna Kwok, engineering manager at Netflix⁠

⁠

Michaela Taylor, head of sales at ShipMonk⁠

⁠

Julie Ruehl, CFO at Fly Leasing Limited⁠

⁠

Alli Young, head of media platform sales at Google⁠

⁠

Raena Saddler, VP of people and managing director at Lean In⁠

⁠

Neha Sampat, CEO at Contentstack⁠

⁠

Gaby Fraga, head of product and technology at the Obama Foundation⁠

⁠

Sunanda Pepalla, chief of staff at Dell⁠

⁠

Beth Steinberg, chief people officer at Chime⁠

⁠

Miriam Donaldson, head of people and organization at Novartis⁠

⁠

Kat Cole, former COO and president of Focus Brands (owns Cinnabon, Jamba Juice, and Auntie Anne’s)⁠

⁠

Jessie Duan, chief of staff to the CTO at Roblox⁠

⁠

Arjun Dugal, CTO of Capital One⁠

⁠

Heath Hohwald, CTO of AlphaSights⁠

⁠

Sarah Montgomery, senior director of strategic accounts at Expedia⁠

⁠

Delaney Manders, VP of engineering at Shopify⁠

⁠

General

Navigating challenges around discrimination

⁠

Michele Godwin, Chancellor professor at UCSD⁠

⁠

Sheree Atcheson, head of D&I at Monzo⁠

⁠

Michelle Glauser, founder of Techtonica⁠

⁠

Dana Levine, account executive at Atrium⁠

⁠

Jarrid Tingle, founder of Harlem Capital⁠

⁠

Siri Chilazi, researcher at Harvard Kennedy School⁠

⁠

Kamala Avila-Salmon, marketing inclusion strategy lead at Facebook⁠

⁠

Archana Gilravi, VP of partnerships at Lean In⁠

⁠

Alice Vilma, head of the multicultural innovation lab at Morgan Stanley⁠

⁠

Yai Vargas, founder of The Latinista⁠

⁠

Hana Mohan, founder of MagicBell⁠

⁠

Finding work life balance

⁠

Maya Topitzer, head of product at LiveBetter⁠

⁠

Jessica Li, head of content at Elpha⁠

⁠

Finding resilience

⁠

Susie Kim, founder of Pluto Money⁠

⁠

Yusra Mardini, Olympian⁠

⁠

Liana Herrera, founder of Bottomless⁠

⁠

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