Startup Failure Analysis Key Lessons from Abby Sugar
A case study of a fantastic founder.

In this episode of Feel the Boot, host Lance Cottrell delves into the startup journey of Abby Sugar, the impressive founder of PlayOut Apparel, a genderequal apparel brand. Despite the brand's promising concept and innovative approach, it ultimately failed. Abby bravely shares her experiences and the unique challenges she faced, providing valuable insights for earlystage founders. Topics covered include founder mental health, team dynamics, investor relations, and the impact of external market factors. This indepth conversation offers actionable lessons for anyone navigating the complex world of startups.

Abby Sugar’s Bio:
Having worked as a writer, editor, and independent personal trainer, Abby Sugar is a lifelong learner and taught herself about fashion, business and startups after studying English Literature in college. Abby is a graduate of Barnard College, Columbia University, and studied abroad at Hertford College, Oxford University.
To Abby, learning is everything, and her life motto is f*cking figure it out – so she set out to build the brand that she and her cofounders wish existed when they were younger. As an outgoing, unapologetically queer startup founder, she strives to be a leading voice in and for the LGBTQ+ community. Abby founded Play Out Apparel in 2018 with her cofounder, Grey Leifer. As Play Out's CEO, Abby:
Graduated from the Founder Institute as a Select Portfolio Company
Raised $750K in preseed from missionaligned investors and secured loan opportunities
Won $20K from the National Business Inclusion Consortium’s pitch competition and $10K from Alibaba and HelloAlice (chosen as 1 of 50 winners from 12,000 applicants!), as well as winning other pitch competitions
Shared her story in the New York Times and Forbes
After an incredible journey, Abby closed Play Out Apparel in 2024 to pursue other opportunities as a startup founder, consultant, and investor.
Abby was named to the Forbes Next 1000 List in 2021, she speaks on podcasts, international panels, and gives frequent interviews about startups, fashion, diversity and inclusion, and topics important to LGBTQ+ individuals.
Be sure to SUBSCRIBE to Multitudinous Musings, Abby's monthly Substack Newsletter, where she shares general educational articles about startups and investing, longform journalism, and poetry/literature that she reads it's also known as Sugar's Recommended Reading. https://abbysugar.substack.com
LinkedIn   / abbysugar  
Instagram   / a.n.other.sugar  

Blog https://ftb.bz/107B
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00:00 The Cult of Successful Founders
00:57 Introducing Abby Sugar and PlayOut Apparel
04:07 Challenges and Insights from PlayOut's Journey
07:37 Fundraising Struggles and Market Realities
16:21 Team Dynamics and Operational Hurdles
31:34 Financial Struggles and Business Loans
32:02 Challenges of Fundraising for Underrepresented Founders
33:33 Investor Expectations and Operational Hurdles
37:37 The Mental Health Toll on Founders
44:34 Lessons Learned and Moving Forward
53:44 Final Thoughts and Future Plans
57:44 Conclusion and Call to Action


Lance Cottrell has been an active startup advisor and startup mentor for over a decade.
He has helped countless startups navigate the key decisions of their journey, like when to take venture capital investment and negotiating term sheets.
He works with many companies in accelerators like Y Combinator and Founder Institute.
He provides help with startup funding including raising venture capital and angel investment.
He can help you achieve liquidity for your company at a high valuation.
Feel the Boot is a startup vlog of tips and advice for earlystage founders.