The Messy Parts: Build a $22M Company While Surviving Layoffs, Lawsuits, Losing Friends

Guest: Jaclyn Johnson (Founder, Create and Cultivate)

Host: Maryam Banikarim
Air Date: October 19, 2025

Episode Overview

This episode explores the "messy parts" of Jaclyn Johnson’s remarkable entrepreneurial journey—best known as the founder of Create and Cultivate—highlighting the setbacks, personal losses, betrayals, layoffs, and lessons learned that fueled her eventual success. Host Maryam Banikarim goes beyond the headlines to unearth the unseen struggles behind a $22 million company exit, making this an honest, high-energy discussion about resilience, reinvention, and redefining the meaning of success in women-led businesses.

Key Discussion Points & Insights

1. Origins of Ambition and Work Ethic

• Parental Influence: Raised in a family of entrepreneurs, Jaclyn attributes her drive to her parents’ tireless hustle.
  • “My dad is sort of sales and like the marketing side. My mom is like the financials backend admin. So I got to see both worlds in action.” (01:57)
• Early Independence: Started working multiple jobs in high school for independence—a self-starter mentality that would shape her career.

2. Early Career: Navigating Setbacks and Discovering Strength

• Magazine Dream Deferred: Landed her “dream job” as junior editor at Allure only to turn it down due to an unlivable $22k salary:
  • “I can’t survive on makeup.” (03:08)
  • Turning down the role wasn’t a moment to fold; it became a motivator to prove her worth.
    • “I do really well when people tell me no or say I can’t do something, like, it’s actually the best medicine for me.” (04:21)
• Internship Marathon: Embraced experiential learning through numerous internships and learning all functions in media led her to understand “how things really work.”
  • “If you want to be an entrepreneur... you kind of have to do every role at that business at some point.” (05:51)

3. Inventing (and Reinventing) Herself in Digital

• Craigslist Leap: Landed a pivotal job at an early social media agency via a questionable Craigslist ad (06:16).
• First-Mover Advantage: Helped major brands like MAC and Estée Lauder get online before social was mainstream.
  • “We should get on the forum, send it to them early... doing what would be an influencer campaign before they were called influencers.” (08:14)
• Building Confidence: Advocates for “fake it till you make it,” noting most success stories include quiet failures:
  • “You might not be the expert today, but you can be the expert tomorrow.” (09:50)
  • She’s described as “relentless,” owning the word as a badge of entrepreneurial honor. (10:16)

4. The First Legal Mess: Friendships & Lawsuits

• Friendship Fallout: Naively helped “poach” a friend for a competitor, resulting in her employer being sued (11:26)
  • “I’m being sued. I’ve made it.” — addresses the scary, character-building experience with humor (12:54)
• Hard Lessons: Major takeaway is being “relentless” under pressure, and working harder as a coping mechanism for anxiety. (13:03)

5. Turning Rejection (& Layoffs) into Redirection

• Layoff & Relocation: Facing layoffs during the 2009 recession, she moved (reluctantly) from NYC to LA to keep a job, embracing change.
• Culture Clashes: Found herself out of place at Citysearch and ultimately was fired due to her out-of-the-box, high-velocity approach.
• Advice for Others:
  • “Rejection is redirection. I fully believe that I would have never started a company had I not gotten laid off.” (19:17)

6. The Accidental Entrepreneur: Birth of ‘No Subject’

• Serendipitous Agency Start: Landed her first client by bluffing that she had an “agency” (which she and her partner then created overnight).
  • “He was like, hire my agency, which did not exist. And he was like, fly to New York and pitch me. So literally, we, like legal zoomed a company.” (19:51)
• Mother as Unofficial Co-founder: Her mom handled QuickBooks for years—even when private equity came knocking (20:59).

7. Partnership Breakups and Losing Her Community

• Financial Betrayal: Discovered business partner’s financial mismanagement—a devastating personal and professional blow.
  • “There was a real betrayal... I had to tell all of our clients. But it became like this me versus everyone else sort of scenario. I lost a lot of friends.” (27:59)
• Mental Health Toll: Suffered panic attacks, anxiety, loneliness, and the heavy burden of running the business solo:
  • “From 23 on till 36, 37, I was heads down working, like to a very unhealthy degree.” (29:43)
• Turned to medication and hard work as coping strategies.

8. The Rise of ‘Create and Cultivate’

• Side Hustle Genesis: The “creators’ getaway” at the Ace Hotel, Palm Springs (2011) began as a low-budget side project:
  • “We were so broke... Levi’s became the presenting sponsor. It made all the difference.” (23:54)
• Scaling Up (2011-2016): Kept it a scrappy side project for four years, quickly growing from 25-person events to 300+ and building a “cool girl” brand via smart sponsorships (Warby Parker, Levi’s).
• Big Pivot to Full-Time: Brought on Raina Panchansky as partner in 2016; event momentum exploded.
  • “After that first event in 2016, the momentum was crazy.” (32:23)
• Unusually High Margins: Outsized profitability for an events business (50% margin per event), achieved by doing everything in-house (33:05).

9. All-Female Teams and the Power of Community

• Built a women-first ecosystem, especially during the rise of #MeToo:
  • “What a utopia… Like, the attendees are women, the caterers are women. Everyone we work with is women.” (34:09)
• Contrasted with earlier toxic, competitive workplaces; now focused on supporting, not gatekeeping.

10. Exit, Burnout, and New Beginnings

• Nearly Sold for $75M: In 2020, Create & Cultivate was on track for a huge exit until the pandemic wiped out live events, slashing valuation to $22M (33:05, 35:15).
• Pivoted Rapidly to Digital: Launched digital events and revenue streams within weeks. (35:15)
• Honest about Burnout: Candidly describes losing her passion, feeling “creatively depleted” and depressed after COVID chaos.
  • “I was, like, pushing through on all, firing on all cylinders.” (37:51)
• Final Sale: Ultimately sold to private equity, meeting her number but recognizing it wasn’t her dream exit (37:53).

Notable Quotes & Memorable Moments

• On Rejection:
  “Rejection is redirection. I fully believe that.” (19:17) — Jaclyn Johnson

• On Ambition:
  “I do really well when people tell me no or say I can’t do something, like, it’s actually the best medicine for me.” (04:21) — Jaclyn Johnson

• On Partnership Breakups:
  “There was a real betrayal...I lost a lot of friends...I was like, I’ve lost my friends now. I have this business on my own. And it felt like extremely isolating.” (27:59) — Jaclyn Johnson

• On Fear and Risk:
  “What’s the worst that could happen? It fails, you shut it down. Who cares? Like, you can figure it out.” (21:56) — Jaclyn Johnson

• On Career Advice:
  “I think this idea that you have to work your way up in one job...that’s completely gone away.” (38:58) — Jaclyn Johnson

• On Learning Financial Literacy:
  “You have to be involved in everything in your business, and you have to understand the numbers and be obsessed with the numbers.” (27:03) — Jaclyn Johnson

• On Burnout:
  “I wasn’t excited anymore. I was really depressed, to be honest. Everything I had built had changed. The world had changed.” (35:15) — Jaclyn Johnson

Practical Lessons and Career Myths Addressed

• Bootstrap vs. Funding: Wouldn’t bootstrap again if possible, stresses importance of leveraging other people’s cash (39:25).
• Diversify Income: Urges young people not to rely on a single job—her seven-figure return as an early Away investor started as a $10k risk when she was broke (39:57).
• Women and Money: Champion for financial transparency and peer mentoring around wealth, real estate, and leveraging (40:30).
• Team Over Heroics: Success is built on partnership, support, and community—not solo hero journeys.

Timestamps for Major Turning Points

• Dream Job Rejection & “I can’t eat makeup.” — (03:08)
• Friendship Lawsuit/First Major Mess — (11:26)
• Fired After LA Move & “Rejection is redirection.” — (16:26-19:17)
• First Agency Client & Mom as Bookkeeper — (20:59)
• Business Partner Breakup—Social Fallout— (27:01-27:59)
• First Create & Cultivate event and Levi’s Sponsorship — (23:54)
• Going All-In on Create & Cultivate — (25:02, 32:23)
• COVID Crushes Business, Digital Pivot — (35:15)
• Exit and Life After — (37:53)

Final Insights

Jaclyn Johnson’s journey underscores that success in entrepreneurship rarely travels in a straight line. Her messiest experiences—betrayed friendships, lawsuits, layoffs, high-stakes pivots, and personal burnout—not only shaped her resilience but also enabled her to scale, sell, invest, learn, and ultimately redefine what “winning” looks like as a founder and as a woman. Her story is a masterclass in relentless reinvention, candid vulnerability, and practical generosity for others about the realities behind glossy headlines.