What Journey’s Pivot from B2C to B2B Reveals About Enterprise Sales

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. RUNTIME 38:28   EPISODE BREAKDOWN (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. LINKS Stephen Sokoler Journey   SUBSCRIBE   🎧 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 📸 Instagram: https://www.instagram.com/fundbuildscale/   Thanks for listening! – Walter.