Race to Saturn

Overcoming Hurdles Examples


When you’re starting a new company or a new initiative within a company, it’s common to have doubts when you encounter hurdles. And these doubts can be fundamental. You may regularly encounter events that make you doubt whether your startup can succeed.

That’s normal! Facing roadblocks as you build something new doesn’t mean your company is doomed. In fact, facing near-company-ending roadblocks is a common experience that many (maybe most?) now successful companies have had.

But it’s easy to forget that.

So here are stories of now successful companies that faced hurdles that seemed at the time like they could (or maybe should) end the company.


Federal Express (FedEx)

Federick Smith started Federal Express in 1971 to provide a better way to do airfreight shipping.

But his first business model was much more focused.

Smith found out how inefficient it was to ship money across the country, and how much those inefficiencies cost the financial system. He created a plan to tackle these inefficiencies using air transport, and he pitched it to the U.S. Federal Reserve (the Fed, which oversees the U.S. banking system).

The Fed’s initial response was positive, and it (seemed to be) committed to the project. Smith took that as enough to call his company “Federal Express”—not just because “Federal” sounded official but also because the business was going to be, basically, built around serving the Fed.

Smith moved forward investing his own money and that of friends and family in purchasing airplanes.

He was taking a big risk, but with the Fed’s (expected) backing, he determined that it was worth it.

Then: As things were near ready to launch, Smith got a call from the Fed. They were backing out of the deal.

In other words, the customer around which Smith had named his company, and structured his company, and had relied on to literally buy planes, was out.

FedEx absolutely could have ended right then.

But Smith took a step back and assessed whether he thought the underlying plan that had inspired him to start the company was still valid. Even without his bedrock customer, he determined that it was. And he moved forward.


History of FedEx

Business Wars (from Wondery): FedEx v. UPS, S40, E1 (August 17, 2020):

  • this episode goes into how FedEx got started. Including that incredible moment when the Fed backed out.

Business Wars (from Wondery): FedEx v. UPS, S40, E2 (August 19, 2020):

  • this episode continues the story of FedEx against the odds beginnings, including how Fred Smith went to Vegas to try and earn enough money to keep the company afloat (incredible story, though not a recommended strategy for others!)


Airbnb struggled for a while to get any kind of meaningful traction, and their struggles are captured in an early investor meeting, as cofounder Nate Blecharczyk recounted in his 2013 Startup School talk.

The founders gathered at a cafe to meet with a well known angel investor. Half way through the founder’s pitch, the investor gets up and leaves. Just leaves. No explanation.

Here’s Nate talking about it:


The founders of Podium had a similar experience of feedback from someone they admired. They had prepped a big pitch to a VC analyst at their office, and were psyched for the chance at a big break. But, 20 minutes into the pitch (a scheduled 60 minute meeting), the analyst gets up, abruptly says he has to go, and just leaves.

A similar experience happened later, with a leading VC investor they admired. 5 minutes into the pitch, he stopped them and said bluntly: I think your business model won’t work, and you are going to fail.

Here’s founder Eric Rea talking about it (this starts at the first story, the second story starts at 8:45):


Boxed, an online wholesale store valued at around $900 million, provides one more story of skepticism from investors.

Founder Chieh Huang and his cofounders had sold a video game company, so had a track record to attract investors. One investor had told them that he would invest in their next company, without knowing what the company was about.

Then, Chieh had a meeting with the investor, and excitedly told him the plan to build an online wholesale grocery store. The investor’s response: I would have given you a check without knowing your idea. But this is the dumbest idea I’ve ever heard. I have a fiduciary duty to my partners. Now that you’ve told me you’re idea, I can’t in good conscious invest with you.

Here’s Chieh relaying the story on How I Built This (story at 48:00):


Ring is a security system for your front door, purchased by Amazon for over $1 billion in 2018.

When founder Jamie Siminoff was ready to launch his product (originally called “DoorBot”), he was able to land a slot on the show Shark Tank to pitch it. He didn’t land a deal on the show, but when the episode aired in November 2013, he got hundreds of thousands of dollars in orders for that Christmas (Ring eventually made millions from that appearance).

So in early December, they started shipping the product for the first time to a mass audience.

So far so good. Except, the team had changed a few items in the software prior to shipping thousands and thousands of them. The problem, which they would only realize later, was that the software wasn’t applied right. The result was garbled code on the units.

When people started receiving their units, they discovered that the key feature of the product–the ability to see video of whose at your front door–was not working (there was no picture at all).

When the team realized their mistake, they tried to fix the software. But–as they learned on Christmas eve of that year–they could not change the software on any units in the field. So their big shipments of thousands of units to their first mass group of users, on Christmas, were duds.

They didn’t have a way of fixing the products. They didn’t have a way of getting the products back. And they had no cash to issue refunds.

Siminoff recounts his clear feeling at the time: “Basically, the business is over.”

Resigned to his fate, Jamie went out to dinner.

And then he had an idea. He recalled that a few weeks beore they had changed servers–getting rid of a more complicated one for a streamlined option. The thought–could they put the old server back online as a way of processing the videos on the products in the field.

He called his engineer, who worked through the night to give it a shot.

And it worked. The restored server was able to process the video on the units. They let the customers know that they could update their units–and the videos were good to go. And the business could survive.

Here’s Jamie recounting the story on How I Built This:


Figma is an extremely successful startup that creates a way for designers to work on designs together in the browser. Their June 2021 venture raise valued them at $10 billion:

But they faced significant pushback in their earlier days, from the very users they were going after. Cofounder and CEO Dylan Field tracks Figma’s story here:

The big pushback came from Figma’s idea that you should make it easy for people to collaborate on design, and do it in the browser. Field writes:

We didn’t realize that launching Figma was heresy, a generational assault on top-down, siloed models of decision making and a challenge to the identity of many designers. While some immediately understood the potential of building design software in the browser, our vision elicited an immediate and negative reaction from others. Some even told us that if this was the future of design, they were changing careers.

That is a pretty brutal response from people in your target audience. But Figma persisted.