Meet Diana!

Discover how Diana Gleason transitioned from a professional dancer to building a thriving six-figure accounting firm, and her insights into scaling a service-based business, leadership, and personal growth.

Main Topics:

- Diana’s unconventional path from dance to accounting

- Building and scaling DG Accounting Agency

- Leadership, systems, and operational strategies for growth

- Balancing entrepreneurship with family life

In this episode:

- Diana shares her inspiring story of pivoting careers and establishing her firm

- Key lessons learned from scaling her business and building a team

- How her background in dance instilled resilience and discipline

- Practical strategies for creating systems and empowering employees

- Her vision of the future: becoming CEO and eventual business sale

Timestamps:

00:00 - Introduction to Diana Gleason and her unique journey from dancer to accountant

01:05 - Celebrating five years in business and recognizing milestones

02:12 - Evolving roles within her firm and operational growth

04:56 - How a leadership program with Gary Vaynerchuk influenced her mindset

09:45 - Leadership style adjustments for team empowerment

16:44 - Balancing motherhood and entrepreneurship while managing physical health

24:47 - Connecting with her passion for supporting dance studios and small businesses

27:29 - Her mission to humanize accounting and provide judgment-free financial support

32:09 - The value of honesty combined with compassion in client conversations

34:45 - Recognizing warning signs of potential business trouble

37:39 - Insights into her leadership program with Gary Vaynerchuk at VaynerX

45:17 - Day in the life: balancing family, business meetings, and sales efforts

48:24 - Future goals: becoming CEO and eventually selling her firm

51:02 - Personal interests, hobbies, and the importance of continuous growth

54:50 - Rapid-fire segment: dream vacation, favorite tech, and more

Connect with Diana:

Personal Instagram - https://www.instagram.com/dianagleason/

LinkedIn - https://www.linkedin.com/in/dianagleason/

Meet Cash!

Discover how Cash East transitioned from a childhood love of fly fishing to building innovative software tools that revolutionize real estate investing and bookkeeping.

Gain insights into the importance of data, the value of trusting a team, and embracing risk to grow professionally and personally.

In this episode:

- Cash shares his unique family history and the story behind his distinctive name, Cash.

- How his childhood passions led him into entrepreneurship and environmental science.

- The evolution from environmental consulting to environmental accounting and software development.

- The critical role of data, discipline, and teamwork in his success.

- The influence of habits, travel, and outdoor hobbies on his professional journey.

- Vision and short-term goals for his innovative software and investment projects.

Timestamps:

00:00 - Introduction to Cash East and his intriguing family history

01:26 - Childhood experiences and family influences on careers

02:04 - The story behind the name "Cash" and its impact

02:25 - Early career in finance, accounting, and environmental consulting

03:16 - Transition from biology to environmental business models

05:02 - Starting entrepreneurial ventures in fly fishing gear

11:11 - Balancing family and professional pursuits

13:03 - The attraction of entrepreneurship and control over destiny

14:25 - Using data and models in supply chain and environmental work

17:43 - Challenges in making data understandable and actionable for business owners

20:01 - Entry into real estate investments and learning to analyze deals

26:35 - The mindset needed for taking calculated risks and big swings

28:19 - The importance of data and trusting the right people in decision-making

32:11 - Surrounding yourself with reliable partners and team members

37:41 - Transitioning to managed properties and improving operational efficiency

41:04 - Creating a unified platform for bookkeeping and financial oversight

43:15 - The role of AI in automating tasks and freeing up entrepreneurs' time

45:54 - The value of time back from automation and AI tools

49:05 - Short-term goals: expanding the bookkeeping tool and community engagement

50:29 - Embracing AI growth and upcoming opportunities in tech

51:07 - Rapid fire questions: favorite books, exercise, travel preferences, tech tools, and final meal

Connect with Cash:

Personal X - https://x.com/CashionEast

Kestrel - https://kestrelrms.com/

Meet Jeff!

Explore Jeff Okrepkie's inspiring story of resilience, community rebuilding, and servant leadership, shaped by personal tragedy and dedicated public service.

This conversation delves into his unique approach to leadership, built on humility and a profound sense of community obligation.

In this episode:

- Jeff shares how experiencing the Tubbs Fire in 2017 transformed his life and propelled him into public service.

- Insights into the importance of ground truth and humility in leadership, especially during crises.

- The role of community-led recovery initiatives like Coffey Strong and how grassroots efforts can inspire systemic change.

- Practical advice for citizens eager to get involved locally, emphasizing volunteerism and stepping out of comfort zones.

- Strategies for leaders on managing ego, fostering teamwork, and making informed decisions grounded in real-world experience.

- Jeff relates his insurance expertise to his public decision-making, highlighting risk analysis and community safety.

Timestamps:

02:21 - How losing his home in the Tubbs Fire catalyzed community efforts

04:34 - The grassroots creation of Coffey Strong neighborhood recovery model

07:54 - Jeff's transition from community volunteer to city council member

09:12 - Lessons from early government work with Senator John McCain

14:10 - Emotional toll and community support after disasters

17:42 - Applying lessons learned from fires to local policy and community resilience

21:44 - The influence of family background on Jeff’s service philosophy

27:11 - The importance of humility and teamwork in leadership success

29:05 - Leadership lessons: Ego, humility, and surround yourself with experts

33:47 - Balancing a day job in insurance with public service responsibilities

37:11 - Jeff’s journey in the insurance industry, shaped by economic downturns

44:20 - Balancing family, sports, and travel with civic duty

47:09 - Rapid fire: Dream vacation, favorite books, and childhood memories

The insights from Jeff’s personal story underscore that leadership often emerges from adversity, grounded in humility, service, and a passion for community resilience. Whether tackling local wildfire recovery or engaging in civic duties, his journey exemplifies how purpose-driven by legacy and values can inspire actionable change at every level.

Connect with Jeff:

Personal LinkedIn - https://www.linkedin.com/in/jeffokrepkie/