The Upside

How My Five Business Failures Led to a Win

I had five business failures before finally landing on a winner. Here’s why I have no regrets.


It’s funny to me how people always look at others’ business success as a single phenomenon or an overnight success story. But ask just about any entrepreneur how they made it big and you will hear stories of the many failures they had before finally getting it right.


And my story is no different.

Here are five business failures that have shaped me as an entrepreneur, and that ultimately led me to building my most prized venture, The Upside.

Before there was Groupon, there was Daily Candy and Social Sip. Well, almost.

In 2004 I came up with the idea for a business I called Social Sip: a daily morning email highlighting one fun and inexpensive activity to do in NYC each day, plus a discount to purchase tickets. My revenue plan was to sell ad space and newsletter content to local restaurants, bars, etc. in the surrounding area of the daily promoted event.


I loved the name, the ad strategy and marketing plan behind the idea. But I knew the business would need the type of backend technologies that were largely unavailable at the time, and that required coding. I couldn’t find someone to partner with me on the tech, so I never even got it off the ground beyond a logo and URL.

If Le Sport Sac had a baby with Birchbox…

In 2005 I launched 80Mad, a handbag line for the on-the-go modern woman. Each bag came with a matching cosmetic case filled to the brim with free beauty product samples.


Beauty companies needed a targeted way to get their product samples into the hands of potential customers. My target audience loved receiving free gifts. It was a win-win and I had companies lined out my door (and boxes of product lined up my apartment walls) to place their product samples in those cute 80Mad bags.


Of course, this was before Facebook or Instagram, and before Warby Parker put DTC-style businesses on the map. Which meant, to make a real profit I needed volume. The only way to do that? Sell to department stores. For anyone who comes from a retail background, you know first-hand what a nightmare this was for a small brand like mine.


Bootstrapping a handbag company in the early 2000s was virtually impossible. And I didn’t have access to an investor. Plus I had a misaligned business partner, so I folded the company after just 12 months in business.


Five years later in 2010, Birchbox launched and the sample industry was forever changed. Looking back, I wish I had focused on the sample program instead of the handbags. Big fail.


The billion-dollar business I almost launched, but didn’t.

After closing down 80Mad in 2006, I had this lightbulb moment: Why did I need to keep spending $200-$300 on formal dresses to wear to weddings when I would only really need to wear each one 1 – 2 times? Women should be able to rent dresses! (see where I’m going here?)


The biggest contact I had in the fashion industry was an ex-boyfriend, and I had no interest in partnering up with him on a new business. I knew that without deep pockets (I had none) or deep connections in that industry (also none), I had nothing to leverage to make it a reality. It was just an idea without legs to stand on.


So I let that idea go, and three years later Rent the Runway launched. Today RTR is valued at $1 billion. Sigh.

Try selling a completely new concept to the hospitality industry.

In 2009 I launched a company that provided turnkey experiential branded suites and high-end swag bags as a way for hotels to earn extra revenue via advertising dollars and to elevate the guest experience.


Imagine checking into a hotel and being handed a reusable tote bag filled with products? Or being invited into the “Sephora Suite” to test out products and receive samples to take back up to your room?


But proving the concept to hotel GMs was a frustrating uphill battle. Plus, I didn’t have enough resilience (or connections) to make it work. I quickly moved on after just three months.


I still love the idea though.


The original Upside concept failed.

When I launched The Upside in 2017, I envisioned a company that acted as a talent agency for professionals who wanted to consult, but didn’t have the skills or confidence to generate and close premium clients.


As I matched clients and consultants, I learned that no matter how many clients I threw their way, a consultant can never build a respected, consistent business if they don’t know how to generate and close clients on their own. I was only providing a bandaid.


So I kept the name, but closed down that entire business line and relaunched as a collective to help consultants advance their business and thrive through unmatched tools, online events and networking.


Three years later we’re still going strong, growing quarter after quarter and most importantly, I love the momentum and look forward to going to work every single day. And what’s better than that!

Failures shape you as an entrepreneur.

Without these previous failures, I wouldn’t have started consulting and I wouldn’t have been driven to launch The Upside.


All of those failures taught me important lessons, like the importance of starting a business that leverages skills and connections you already have. And picking business partners that are perfectly aligned with your values and compliment–not overlap–your skills and networks. And having resiliency. Lots and lots of resiliency. And knowing that there are going to be bumps in the road. And not every day is going to be a win.


For anyone who has ever felt like a startup failure, I encourage you to get back up and try again when the timing feels right.


If I didn’t keep trying, who knows what kind of corporate treadmill I’d be on, punching the clock day in and day out, helping to make other people wealthy instead of building something of my own.

Want to start or grow your consultancy? Check out these Upside resources:

Erin Halper

About the Author

Erin Halper is the founder and CEO of The Upside and the leading authority on independent consulting. Since launching The Upside in 2017, Erin has helped thousands of professionals transition from corporate life into consulting to achieve flexibility, autonomy, and a renewed sense of purpose in their careers.

Erin has been a frequent speaker at Columbia, NYU, Harvard, and Brown and has been featured as a leading future of work expert on dozens of podcasts as well as in Forbes, Business Insider, Nasdaq, Crunchbase and many more.

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