In this conversation, Angela, co-founder of Shepherd, shares her journey from the initial concept of creating flexible work opportunities for parents to evolving into a platform for fractional leadership. She discusses the challenges of bootstrapping, the importance of co-founders, and her vision for the future of work. The conversation highlights the role of AI in enhancing client services and the joy of building a business that aligns with personal values and lifestyle.

Takeaways

• AI can enhance client experiences in various ways.
• The origin of Shepherd was inspired by personal experiences as a parent.
• Flexibility in work is essential for many professionals today.
• The transition from a mom-focused platform to fractional leadership was necessary.
• Bootstrapping presents unique challenges but also opportunities for growth.
• Prototyping and testing ideas with real clients is crucial.
• The future of work is evolving, and Shepherd aims to lead in fractional jobs.
• Having a co-founder can alleviate the loneliness of entrepreneurship.
• Validation comes from real-world feedback and revenue.
• Google Maps symbolizes exploration and spontaneity in life.

Chapters
00:00 Exploring AI in Client Services
01:20 The Birth of Shepherd: A Personal Journey
05:32 Evolving from Moms on a Page to Fractional Leadership
10:11 Challenges of Bootstrapping and Balancing Work-Life
12:19 Vision for the Future: Shepherd's Growth and Direction
16:43 Advice for Founders: The Importance of Co-Founders
19:14 Fun Insights: The Role of Google Maps in Life

Find out more about Shepherd at www.heyshepherd.com
Connect with Angela on LinkedIn: linkedin.com/in/angcatalan

In this conversation, Johan interviews Angela Catalan, co-founder of Shepard, a platform helping startups connect with top-tier fractional talent. Angela shares how her journey into flexible work began with motherhood and quickly evolved into building a marketplace for experienced operators looking for meaningful, part-time roles.

She unpacks the scrappy early days of prototyping Shepard, the challenges of bootstrapping while balancing multiple roles, and how she tests ideas before writing a single line of code. The conversation also touches on how she uses AI thoughtfully without getting caught in the hype, and what it means to build something people actually want—before the platform even exists.

Angela reflects on the importance of having a co-founder, the emotional resilience required to build something new, and why she believes the future of work is flexible, async, and driven by trust.

In this conversation, Johan interviews Alex Solo, co-founder of Sprintlaw, a legal tech company focused on making legal services accessible and affordable for small businesses. Alex shares the origin story of Sprintlaw, the challenges faced by small businesses in accessing legal services, and how technology, particularly AI, is transforming the legal landscape. The discussion covers the importance of agile development, customer feedback, and prioritizing tasks to enhance product offerings. Alex also reflects on the lessons learned from scaling the business and shares insights on maintaining creativity amidst the demands of entrepreneurship.

Takeaways

• Sprintlaw aims to make legal services accessible for small businesses.
• Many small businesses avoid legal services due to cost and complexity.
• Technology can simplify and reduce the cost of legal services.
• Agile development allows for rapid testing and iteration of products.
• Customer feedback is crucial for improving services and features.
• Prioritizing tasks based on effort and impact helps in resource allocation.
• Quick wins can boost team morale and momentum.
• The future of Sprintlaw involves enhancing lawyer efficiency through technology.
• Investing in growth and awareness is essential for scaling the business.
• Balancing speed and quality is key to sustainable growth.

Chapters
00:00 The Birth of Sprintlaw
02:30 Harnessing Technology for Legal Services
05:55 Agile Development and Customer Feedback
09:32 Prioritizing Tasks and Quick Wins
11:04 Future Vision and Product Development
17:23 Lessons Learned and Founder's Wisdom
20:16 Creative Outlets and Personal Insights