Lessons From Zero to IPO in 2 Years with Scott Case
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Hi everyone 👋
Thanks for subscribing for the very first episode of Lessons From Failures. I literally had this idea in the shower the first Monday of January and put it into motion immediately. I decided that in 2021 I would stop watching youtube or scrolling on instagram all day and start making my own content to put out into the world.
I've had my fair share of failures and learned a lot from them, but I was curious to hear about failure stories of people further along in their career, and so, Lessons From Failures was born.
My first conversation is with Scott Case.
At the height of the first dot com boom, Priceline.com was born. Scott was at the center as the founding CTO of Priceline.com. Today, Scott is the CEO of Upside navigating the turbulent landscape of business travel during a global pandemic.
Main Takeaways
“The #1 thing to do if you want to be a founder and you're in your 20s is spend 6 months selling something over the phone.” - Scott Case
It will serve you throughout the rest of your entrepreneurial journey.
As a founder, you are always selling your ideas to other people to get them to come along the adventure. People need to buy into your vision and believe that you are going to take them there.
The business travel market is down 85% from 2019 levels, but it's not zero.
“It's not enough to have a great product, you need to have a go-to-market strategy to go along with it” - Scott Case
B2B Sales Tips
“If you expect to just give someone a demo or explain what the product is and that they’re just going to magically want to order it from you, then you’re wrong.” - Scott Case
Ask for the order 3 times throughout your conversation.
Sales is about building an authentic relation with people. Find out what they care about, what they are trying to accomplish, and how does your product or service accomplish that.
Selling is a numbers game. You can make 100 calls, have 5 people answer, and make only 1 sale, but that's what it takes especially in the enterprise space.
On Founding Priceline.com
“It was crazy. We launched, I think, 8 or 10 products in a year. And so from the time we launched our first product to the time we basically went public, it was a year.” - Scott Case
Scott started working on Priceline with his co-founder Jay Walker in 1997, launched the first product in 1998, and went public in 1999.
Biggest Mistake During Priceline
Didn't understand the difference between leadership and management
Management is about tasks, planning, and deadlines. Leadership is about connecting with human beings and inspiring them to want to execute on the plan you've laid out.
You have to be investing in the team's well-being and what they want to accomplish as individuals.
Help them build out their team that they feel comfortable being effective with as well.
It's hard. It's communication. It's relationships. You need to understand them well.
Stick With Your Principles
Scott decided to keep his team together and not lay-off his team like others in the travel industry. He stayed true to his beliefs and the culture he created at Upside.
The people on the team mattered more than anything and the leadership team decided to do the right thing.
The result was the team stayed strong and worked hard to identify new opportunities in the face of a global lockdown to stay afloat. They took an offensive approach by being proactive in the travel industry as they push through to the end of 2021.
1̶0̶ ̶m̶i̶n̶ ̶12 min highlight reel
There was so much good content that I couldn’t cut it down to a 10 minutes, so here is an extra 2 minutes for you.
There is a ton more information in the full interview. To listen to the full 30 minute interview on your favorite podcast platform click below 👇🏽
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Thanks to Scott Case for always being generous with his time and being the first interview of Lessons From Failures.
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