Ep#25: Scale or Shatter? Why Founders Break

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Startups Decoded

Andy Walsh

41 episodes

22 hours ago

Jaclyn Johnson is a powerhouse entrepreneur, investor, and advocate for women in business.By 35, she had already launched and sold two multimillion-dollar companies, including Create & Cultivate, a first-of-its-kind platform for female entrepreneurs that scaled to eight-figure revenue and partnered with Fortune 500 brands like Amazon, Mastercard, and Microsoft.Now, she’s back with Cherub, a double-sided marketplace designed to bridge the gap between underrepresented founders and democratizing access to category-defining companies. As both an angel investor and advisor, Jaclyn has backed businesses like Away, Live Tinted, and Chillhouse, bringing hard-won experience from her own journey into the founder–funding relationship.Subscribe nowIn this conversation, we break down:Jaclyn’s origin story: why she built CherubHow she approaches angel investing and the lessons she’s learnedWhat makes a great angel pitch (and what doesn’t)The realities of being an accredited investorWhy representation in funding isn’t just moral, it’s market-changingChapters00:00 The Importance of Angel Investments02:49 Jaclyn’s Journey as a Founder and Investor05:41 Understanding Angel Investors vs. Venture Capitalists08:28 The Role of Angel Advisors11:23 Building Relationships with Angels14:15 The Power of Brand Fame17:25 Cherub’s Mission and Deal Flow20:07 Educating Angels and Standardizing Investments23:13 Creating Effective Fundraising Pages26:12 The Role of Analytics in Fundraising29:04 Onboarding Founders to Cherub32:01 Connecting with Angels: Best Practices35:03 Diversifying the Investment Landscape37:58 The Future of Angel Investing40:35 Special Offers for Founders on CherubGuest BioJaclyn Johnson is the founder of Cherub and creator of Create & Cultivate, which she scaled to an eight-figure exit while reshaping how brands and communities support female entrepreneurs. Named a Forbes 30 Under 30 and an Adweek Disruptor, Jaclyn is an angel investor and advisor to companies including Away, Live Tinted, and Chillhouse. She’s dedicated to making capital and community more accessible for underrepresented founders while equipping the next generation of women entrepreneurs to scale.Who Should ListenFounders raising their first angel roundEntrepreneurs seeking representation and resourcesPeople curious about Angel Investing and how to get startedOperators looking to understand the angel landscapeMusic Credit“Neptuno” – Phondupe (Album: Onykia)Access All Areas.Listen: Apple || Spotify || YouTubeSubscribe: SubstackCommunity & Events: Founders CircleConnect: LinkedInSocials: TikTok || Instagram || XWeb: startupsdecoded.com

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Entrepreneurship

Business,

Investing

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Ep#25: Scale or Shatter? Why Founders Break - Leila Lahbabi

Startups Decoded

54 minutes

3 months ago

Ep#25: Scale or Shatter? Why Founders Break - Leila Lahbabi

Send us a textMany founders are chasing scale, but at what cost? In this episode, Leila Lahbabi shares how purpose-driven leaders can grow thriving companies without burning out or losing themselves in the process. We explore the real tension between being a present parent and an ambitious entrepreneur, and how to build high-performing teams that unlock freedom rather than dependence.Leila LahbabiLeila Lahbabi is a trusted advisor to purpose-driven founders and CEOs, helping them scale their companies without sacrificing their freedom, values, or well-being. With a background in strategy consulting for Fortune 100 companies, five years as an entrepreneur, and a deep foundation in psychology, mindfulness, and personal development, Leila brings a holistic, high-impact approach to leadership and business growth.Her work focuses on building high-performing teams and fostering leadership autonomy, enabling founders to step out of the operational grind and into sustainable, values-aligned growth. Leila is also the author of the upcoming book The Billion Dollar Purpose, which explores how mission-driven leaders can unlock talent, scale impact, and build thriving businesses from the inside out.https://www.leilalahbabi.com/impact-at-scaleSHOW NOTESMusic Credit: "Neptuno" - Phondupe (Album: Onykia)In this episode of Startups Decoded, Andy Walsh speaks with Leila Lahbabi about her journey from consulting to entrepreneurship, emphasizing the importance of scaling without sacrificing personal well-being. They discuss the challenges of balancing motherhood and business, the significance of mindfulness and prioritization, and the need to focus on the hard work that truly drives business success. Leila shares her insights on transitioning from being a Chief Everything Officer to a CEO, highlighting the importance of delegation and adaptability in scaling a business effectively.TakeawaysStarting a business is challenging, especially when balancing multiple roles.Mindfulness can help manage stress and improve focus.It's crucial to prioritize actions that drive results.Balancing work and family requires conscious effort and planning.Entrepreneurs often face burnout due to overwhelming responsibilities.Delegation is essential for scaling a business effectively.Understanding the difference between working hard and doing hard work is key.Investing time and intention in your business leads to growth.Adaptability is a critical factor for business success.Reflection and feedback are vital for continuous improvement.Chapters00:00 Introduction to Scaling Without Sacrifice02:20 Leila's Journey: From Consulting to Entrepreneurship04:54 The Reality of Entrepreneurship and Balancing Roles09:42 Catalysts for Change: The Impact of COVID-1913:00 Finding Purpose and Direction in Business16:14 Juggling Parenthood and Entrepreneurship20:33 The Importance of Mindfulness and Strategy23:15Discover Smarter Investing with the Teaminvest Wealth Builders PodcastExpert insights and proven strategies from Australia's top investors. Build your wealth.Listen on: Apple Podcasts Spotify Back to Episodes

Startups Decoded