Rob Matzkin joins Bradley Jacobs to share his entrepreneurial journey from a $20K weekend parking business at 19 to building and exiting multiple companies. With over 20 years of experience in high-growth SaaS and AI startups, Rob now runs a successful fractional consulting business while maintaining his role in the VC world. The conversation dives deep into the emotional rollercoaster of entrepreneurship, revealing what it's really like when things get hard - the financial stress, the isolation, and the constant ups and downs that no one talks about. Rob shares practical strategies for managing stress and staying productive, including his productivity hacking techniques and the importance of deep work. He discusses why cash is king for fractional executives, how to build trust and rapport with clients, and the power of networking and referrals over traditional marketing. Rob also opens up about his dyslexia and how vulnerability and authenticity have become his superpowers in business. The episode concludes with insights on productizing services and the mindset needed to push through challenging times.

Books mentioned: The Hard Things About Hard Things by Ben Horowitz, Screw It, Just Do It by Richard Branson, Deep Work by Cal Newport

Learn More:Scale your fractional practice: https://mylance.coConnect with Bradley Jacobs: https://www.linkedin.com/in/bradley-r-jacobs/

00:00 - Introduction and Rob's background in SaaS/AI startups

01:45 - Defining purpose in business and entrepreneurship

03:26 - The $20K weekend parking business origin story

05:44 - Key lessons from early entrepreneurial experiences

07:26 - The "just do it" mentality and dealing with regulations

09:40 - The emotional rollercoaster of entrepreneurship

13:36 - Stress management and productivity strategies

16:13 - Planning ahead and creating structure for success

18:22 - What moves the needle for fractional executives

20:46 - Why sales and new business development are crucial

22:31 - Building trust, rapport, and getting referrals

24:07 - Networking strategies that actually work

26:15 - Being an introvert in a networking world

28:26 - The power of vulnerability and authenticity

30:23 - Overcoming fear and getting uncomfortable

32:58 - Productizing services for scalable revenue

34:32 - Final advice: structure, freedom, and persistence

35:43 - Where to connect with Rob Matzkin