How Journy grows

Flew to San Francisco and stacked nine investor meetings into 2 days. Every investor knew she was only in town for 2 days to meet investors, so each knew that if they didn't move, someone else would. Her rule: don't start fundraising until you can create competition for the deal and have the meetings back-to-back; investors show growth signal (a lot of growth in a short time), not a magic number, and without a competing offer they keep asking for more data and drag things out.

To find jobs for her team, reached out to a bunch of companies; 3 days later Hopper made an acqui-hire offer. Used it to get Expedia to offer to buy the whole company for a lot more, then brought in Lonely Planet, which offered more still. Went back to Hopper: 'we'd rather go with you, we're more excited about your vision, but you're going to have to pay double now.' Existing investors then also offered to recap the company and lead a new round.

Launched Journy targeting tech-savvy millennials, driven by a mission to democratize luxury travel planning, and charged $6 per trip day for planning. Later pricing was a flat $25 or $50 per day.

Tried to raise money for Journy before she had figured out a growth engine, tracking every pitch in a spreadsheet over about 6 months, sometimes four meetings a day.

When COVID killed travel, tried pivoting Journy to B2B, from international to domestic travel, and to virtual online experiences, while trying to raise more money from existing and new investors.

Spent a lot on marketing and PR, expecting a media article to make everything work. No specifics given on what was bought.