Journey founder and CEO Stephen Sokoler appeared on Fund/Build/Scale in June 2024 to talk about how his startup pivoted from B2C meditation services to a B2B mental health platform, along with what that shift revealed about selling to enterprise clients. He breaks down the challenges of high customer acquisition costs, the trade-offs of venture capital, and the key lessons founders should know before making a major business model shift.

(2:20) Why Stephen decided to found Journey — identifying the need for accessible mental health solutions.

(5:07) “We probably had five or six different products that worked and didn't work until we got to where we are today.” Lessons from early iterations and failures.

(7:32) Pivoting to B2B “was definitely a safer bet than to continue doing consumer, which just seemed like a dead end.”

(9:26) Landing early customers like Warby Parker — how this helped de-risk Journey for enterprise clients.

(11:37) Why he sought out venture capital in the company’s early days — and what he learned from the process.

(13:56) Knowing what he knows now, would he still have pursued VC?

(17:11) Reaching product-market fit “changes the fundamentals of the business significantly.”

(19:00) “One of our core pillars is that it's a global offering rooted in diversity and inclusion.”

(23:17) We think it's really important to make mental health part of the fabric of working at a company, versus a random benefit.”

(25:17) The three key data points Journey tracks to measure impact and effectiveness.

(28:25) “You can decide: Do you want it to be a lifestyle business? Do you want it to be a unicorn?”

(31:49) Work-life balance vs. work-life integration — “I don't like the term ‘work-life balance,’ because then it feels like something's always kind of out of whack.”

(34:29) How Stephen has learned to manage the mental toll of entrepreneurship.

(37:25) “Not every business should be a venture-backed business.” Key insights on whether VC is the right path.

• Stephen Sokoler
• Journey

🎧 Apple Podcasts: https://podcasts.apple.com/us/podcast/fund-build-scale/id1719488387

🎧 Spotify: https://open.spotify.com/show/0EbC8PTUSfpZ4USPC9ErnN

📥 LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/

📓Substack: https://fundbuildscale.substack.com

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Thanks for listening!

– Walter.