Lessons from ‘Failure’ in Startups

Austin Ogilvie
5 min readFeb 16, 2024

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The journey of a startup is often a tightrope walk between success and failure, where timing, execution, and a dash of luck draw the line. Reflecting on the stories of innovative yet ultimately unsuccessful startups provides critical lessons for entrepreneurs of today and tomorrow.

This post explores the stories of four ventures that dared to challenge the status quo!

Kozmo.com, Turntable.fm, Dufl.com, and OutboxMail.com
“Failure” in startups is different than in other industries

Kozmo.com: A Visionary in On-Demand Delivery

Founded in 1998, Kozmo.com was a trailblazer in the on-demand delivery space, promising to deliver VHS movie rentals to customers’ doors in 30 minutes or less. Despite securing approximately $280 million in venture capital, the company struggled with high operational costs and logistical challenges, leading to its closure.

Goodbye message that customers saw on Kozmo.com when the company shut down for good in 2001
Kozmo.com said goodbye to customers in 2001

The legacy of Kozmo.com, however, lives on, inspiring giants like Instacart, Netflix, and DoorDash. Kozmo.com’s story teaches us about the potential and pitfalls of being ahead of your time.

  • Founded Year: 1998
  • Wind-Down Year: 2001
  • Capital Raised: $280M
  • Major Investors: Thomas Weisel Partners, Oak Investment Partners, Flatiron Partners, Hambrecht & Quist

Turntable.fm: Fostering Community Through Music

Turntable.fm created a digital music venue that was both social and interactive, testament to the power of community and music. Despite its innovative approach, the platform struggled to find a sustainable business model amid licensing challenges and a competitive market.

Turntable.fm social music venue UI
Turntable.fm was a social music venue that burned bright for too short a time

The rise and fall of Turntable.fm underscore the importance of a solid revenue strategy for engaging platforms, even when they captivate a large and active user base.

  • Founded Year: 2011
  • Wind-Down Year: 2013
  • Capital Raised: $21.5M
  • Major Investors: First Round, Founders Fund, Union Square, a16z, Jimmy Fallon

Outbox Mail: A Challenge to Snail Mail

Outbox Mail aimed to revolutionize traditional postal services by digitizing physical mail, offering users the option to view their mail online and selectively request physical delivery to their door.

Outbox Mail digitized your postal mail and delivered high res scans via a beautiful iOS app

Outbox’s ambitious venture to disrupt traditional postal services failed due to a combination of factors. Key among these was the misalignment between demand and the high operational costs, rendering the biz model unsustainable.

A significant blow came from a failed partnership with USPS, forcing Outbox to devise a complex and cost-intensive method of collecting mail directly from customers’ mailboxes.

This operational hurdle, compounded by limited market appeal and public perception challenges, ultimately led to the startup’s closure despite its innovative approach.

Outbox Mail digitized snail mail in a beautiful iOS or Android inbox, filtered junk mail, and delivered any parcels or letters physically upon your request. Cofounder, Evan Baehr, pictured above

Outbox’s physical-to-digital bridge underscores the complexities of transforming entrenched habits and industries. The company’s story underlines the importance of navigating external pressures and entrenched interests when introducing disruptive technologies.

  • Founded Year: 2011
  • Wind-Down Year: 2014
  • Capital Raised: $5M
  • Major Investors: Correlation Ventures, Founders Fund, Floodgate

Dufl: Simplifying Business Travel

Dufl proposed an innovative service to manage, clean, and store business travelers’ attire, aiming to simplify travel logistics.

Dufl.com gave users a virtual wardrobe, eliminating the need to pack bags for trips / travel.

Despite its clear value proposition, the service struggled to achieve broad market adoption due to niche demands and operational challenges.

While the service presented a clear value proposition, it struggled to find a broad market due to its niche focus and operational hurdles. Dufl’s story emphasizes the necessity of understanding and scaling to market needs.

  • Founded Year: 2015
  • Wind-Down Year: unclear but seems like 2017 or 2018?
  • Capital Raised: $8.4M
  • Major Investors: unknown

Shyp: Reinventing Shipping

Shyp sought to simplify the shipping process by offering to pick up, package, and send items on behalf of its customers, directly challenging traditional shipping and postal services.

Shyp for iOS made it super easy to mail anything to anyone anywhere in the world. Users could also compare rates, print labels, and track deliveries, etc. across all major carriers

While the company initially received significant user interest and venture capital investment, it faced challenges in scaling its business model sustainably. Shyp’s downfall serves as a reminder of the critical balance between innovation, customer convenience, and sustainable business practices.

  • Founded Year: 2013
  • Wind-Down Year: 2018
  • Capital Raised: Over $50M
  • Major Investors: Kleiner Perkins

Embracing the Lessons of Innovation

The narratives of Kozmo, Turntable, Outbox Mail, Dufl, and Shyp are more than stories of failure; they are testaments to human ambition, resilience, and the relentless pursuit of innovation. These startups set out to solve significant problems with unique solutions, and while they may not have succeeded in the traditional sense, their efforts have left indelible marks on their industries.

For entrepreneurs and investors alike, these stories offer powerful lessons on the risks and rewards of the startup world. They remind us to embrace risk, learn from both history and failure, and persist through adversity, with the understanding that boldness often paves the way to success.

As we continue to navigate the future of innovation, let the courage and determination of these companies inspire us to meet challenges head-on, ever mindful that it is those who dare to innovate who often lead the way to the future.

Thanks for reading !! If you found this post useful, you might also enjoy these:

Founder’s Perspective: Overkill Seed Stage Due Diligence

Accelerators: fantastic…but not magic

Two ways to irreparably f***k up your startup

Streamline digital compliance: https://thoropass.com

Book a 1:1 w/ me: intro.co/austinogilvie to talk startups / investing / moral philosophy

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Austin Ogilvie

currently building Thoropass. fmr CEO of ŷhat (acq by Alteryx NYSE:AYX). YC W15. Bluegrass fan + whitewater kayaker