Carrie Kramer joins Jeremy Bloom on the OhHello.ai pod to reflect on nearly nine years of building Future Proofed, a sales training and consulting company focused on the media and advertising industry. Carrie shares the realities of entrepreneurship, the emotional highs and lows of running a business, the importance of vulnerability in leadership, and the lessons she learned about partnership, values, and progress over perfection.

Takeaways

Building a business means becoming a salesperson, even if you’ve never sold before.
Progress over perfection creates momentum and growth.
Strong partnerships can be the most rewarding part of entrepreneurship.
Vulnerability helped Carrie build trust and credibility online.
Entrepreneurship is often glamorized, but it is not for everyone.
Aligning personal and business values can strengthen partnerships.
Repeat clients are a reflection of trust and strong collaboration.
Leadership requires asking for help and letting go of perfectionism.

Chapters

00:00 Carrie Kramer joins the OhHello.ai pod.

00:40 Carrie explains the evolution of Future Proofed.

03:17 How Carrie and Bo Davis decided to merge businesses.

04:47 The biggest misconceptions about starting a company.

06:52 Learning how to sell for the first time.

08:16 The highs of entrepreneurship and client wins.

10:10 The lowest lows of running a business.

11:50 Leadership lessons and asking for help.

13:24 Why progress over perfection matters.

13:56 Becoming more vulnerable on LinkedIn.

16:01 What Carrie is most proud of after nine years.

18:05 Advice for people thinking about starting a business.

21:04 The importance of personal and business values.

22:48 What Carrie is excited for next.

23:47 Final reflections on growth and entrepreneurship