Spencer Hilligoss is the CEO of Madison Investing - a real estate investment club with bespoke, curated real estate deals. Spencer founded Madison Investing with a singular mission: to help busy, successful professionals invest passively and secure their most valuable asset of all: Time.

By partnering with in-market, vetted operators, Madison Investing has $2.3B in acquisitions, with over 20,000 units. Investors now have access to cash-flowing private real estate syndications and funds, allowing them to enjoy passive returns as these businesses thrive.

Before starting Madison Investing, Spencer was what some consider a “corporate junkie”, growing operations and sales teams in 5 high growth Fintech companies, over the span of 13 years. In 2019, five months before the pandemic, Spencer broke free from the golden handcuffs to give full focus on serving his investment group and growing Madison Investing. Now, as a full-time investor and entrepreneur, he can spend more time with his family and hone his skills on the electric guitar. He is a registered member of FINRA and a member of the Forbes 2022 Real Estate Council.

"It takes a team of people and immense amounts of capital to go and buy these big buildings, improve them, and hold them for long periods of time at a profit."

Key themes included:

1. 1. Investment Goals

      • Consistent income vs. capital growth

   2. Networking

      • Building long-term relationships

   3. Real Estate Strategies

      • Acquiring and managing properties

   4. Financial Benefits

      • Property improvements and exits

   5. Market Timing

      • Impact on investment outcomes

   6. Due Diligence

      • Vetting teams and deals

   7. Passion and Transition

      • From tech to real estate

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Website: http://www.madisoninvesting.com/

Email: spencer@madisoninvesting.com

Phone: 415.290.0328

LinkedIn: https://www.linkedin.com/in/shilligoss/

—

Follow Dana on LinkedIn: https://www.linkedin.com/in/danabrobinson/

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—

If the information in these conversations and interviews have helped you in your business journey, please subscribe to the show, and leave me an honest review.

Your reviews and feedback will not only help me continue to deliver great, helpful content, but it will also help me reach even more amazing entrepreneurs just like you!

*Some of these links might be affiliate links. Thank you in advance if you choose to work with one of the companies I believe in. The money I make from your purchase helps to keep the content you enjoy, and rely on to grow your own business, free to you.

Thanks for tuning into this episode of Exit Plan!

Ryan Duffy is a seasoned entrepreneur who effortlessly leverages his extensive background in Hollywood and tech to drive innovation. He started with a small team at Vidme, ultimately cultivating a company philosophy that prioritized careful, methodical growth.

Through numerous ventures, including pioneering an early NFT platform and founding the audio course platform Knowable, Ryan has faced and overcome countless challenges. Now at Medium, he continues to draw from his rich experience to navigate the creator economy with his latest venture, Stack.

"One of the hardest things I've ever had to do professionally...trying to explain what an NFT is. And if you think about it, it's like, it's digital, but, like, you own it."

Key themes included:

1. Early NFT Platform Struggles

2. Knowable's Audio Course Challenges

3. Pandemic's Impact on E-learning

4. Vidme's Monetization and Infrastructure Issues

5. Transition to Medium

6. Leveraging Career Skills and Experience

7. New Venture Focused on Creator Economy

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Website: www.duffy.work

Contact: https://duffy.work/contact-form

LinkedIn: https://www.linkedin.com/in/ryanpatrickduffy/

—

Follow Dana on LinkedIn: https://www.linkedin.com/in/danabrobinson/

Follow Dana on Instagram: https://www.instagram.com/danarobinsonofficial/

Subscribe to Dana’s weekly newsletter at https://www.danarobinson.com

—

If the information in these conversations and interviews have helped you in your business journey, please subscribe to the show, and leave me an honest review.

Your reviews and feedback will not only help me continue to deliver great, helpful content, but it will also help me reach even more amazing entrepreneurs just like you!

*Some of these links might be affiliate links. Thank you in advance if you choose to work with one of the companies I believe in. The money I make from your purchase helps to keep the content you enjoy, and rely on to grow your own business, free to you.

Thanks for tuning into this episode of Exit Plan!

Matt Rinkey is a wealth advisor and certified exit planner who specializes in helping entrepreneurs and real estate investors maximize their business value and achieve their financial goals. With a background in family office, hedge fund, and real estate, Matt brings a wealth of experience to support his clients in building the right strategies for wealth creation and life aspirations.

Through his boutique team's comprehensive approach and flat fee model, Matt serves as a valuable resource for entrepreneurs, providing guidance on day-to-day financial questions and major life-altering events. His expertise focuses on integrating personal and business planning, exit planning, and creating customized investment checklists to help clients prioritize their business growth and avoid common pitfalls.

"So how do we make them better as investors? And that's just not by, hey, send your money here."

Key themes included:

1. Gaining expertise from clients and members

2. Entrepreneurial strategies for tax planning

3. Evaluating financial team and wealth creation

4. Exit planning and maximizing business value

5. Investing based on core values, checklist

6. Integrating personal aspirations with business goals

7. Importance of early planning for entrepreneurs

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Website: http://www.illuminationwealth.com/

Contact: matt@illuminationwealth.com

LinkedIn: https://www.linkedin.com/in/mattrinkey/

—

Follow Dana on LinkedIn: https://www.linkedin.com/in/danabrobinson/

Follow Dana on Instagram: https://www.instagram.com/danarobinsonofficial/

Subscribe to Dana’s weekly newsletter at https://www.danarobinson.com

—

If the information in these conversations and interviews have helped you in your business journey, please subscribe to the show, and leave me an honest review.

Your reviews and feedback will not only help me continue to deliver great, helpful content, but it will also help me reach even more amazing entrepreneurs just like you!

*Some of these links might be affiliate links. Thank you in advance if you choose to work with one of the companies I believe in. The money I make from your purchase helps to keep the content you enjoy, and rely on to grow your own business, free to you.

Thanks for tuning into this episode of Exit Plan!

Lee is a value creation expert, a skill not commonly discussed when it comes to scaling and preparing for exits. I know you listeners would love to hear about his practical tools and insights on this.

Lee is also a 2x bestselling author with over 30 years of experience in the business world and currently the CEO of Execute to Win. He has founded and led seven companies, including Able Aerospace, which he grew from two to 500 employees and 2,000 customers in 60 countries culminating in a 9-figure exit in 2016.

"How would you like to create value in the world?"

Key themes included:

1. Value creation as the key business focus

2. Importance of aligning business model and strategy

3. Benson's methodology applicable to all business sizes

4. Benson's entrepreneurial journey

5. Simplicity and focus in business growth frameworks

6. Criticisms of higher education's lack of practicality

7. Fostering value creation mindset in youth

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Website: www.etw.com

Contact: bo@evancarmichael.com

LinkedIn: https://www.linkedin.com/in/lee-benson-5b6101/

X: https://twitter.com/executetowin?lang=en-GB

—

Follow Dana on LinkedIn: https://www.linkedin.com/in/danabrobinson/

Follow Dana on Instagram: https://www.instagram.com/danarobinsonofficial/

Subscribe to Dana’s weekly newsletter at https://www.danarobinson.com

—

If the information in these conversations and interviews have helped you in your business journey, please subscribe to the show, and leave me an honest review.

Your reviews and feedback will not only help me continue to deliver great, helpful content, but it will also help me reach even more amazing entrepreneurs just like you!

*Some of these links might be affiliate links. Thank you in advance if you choose to work with one of the companies I believe in. The money I make from your purchase helps to keep the content you enjoy, and rely on to grow your own business, free to you.

Thanks for tuning into this episode of Exit Plan!

Brad Baldridge is a financial advisor specializing in college planning, helping families navigate the complex landscape of college costs and financial aid. With a background in engineering, Brad transitioned into financial advising and found his niche in assisting clients with the increasingly challenging task of managing college expenses.

He emphasizes the importance of individualized approaches to college planning, considering each student's unique needs, abilities, and career aspirations. Brad's expertise extends beyond college planning to comprehensive financial portfolio management, offering a holistic approach to financial advising for his clients.

"If you take a $60,000 school and you get 35,000 of scholarships and you're down to 25, that's about where the state school probably is going to be. Either way, you still have to pay 30,000. So that's the next step, right, is how do we pay that efficiently?"

Key themes included:

1. Financial planning strategies for businesses and families

2. Multiple paths to success beyond college

3. Complex situations require early, specialized planning

4. Entrepreneurial lessons from "The King's Fly Swatter"

5. College costs, aid, and efficient payment options

6. Financial aid challenges for entrepreneurs' income assessment

7. Importance of specialized advisors for college planning

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Website: www.tamingthehighcostofcollege.com

Contact: https://tamingthehighcostofcollege.com/contact/

LinkedIn: https://www.linkedin.com/in/bradbaldridge/

—

Follow Dana on LinkedIn: https://www.linkedin.com/in/danabrobinson/

Follow Dana on Instagram: https://www.instagram.com/danarobinsonofficial/

Subscribe to Dana’s weekly newsletter at https://www.danarobinson.com

—

If the information in these conversations and interviews have helped you in your business journey, please subscribe to the show, and leave me an honest review.

Your reviews and feedback will not only help me continue to deliver great, helpful content, but it will also help me reach even more amazing entrepreneurs just like you!

*Some of these links might be affiliate links. Thank you in advance if you choose to work with one of the companies I believe in. The money I make from your purchase helps to keep the content you enjoy, and rely on to grow your own business, free to you.

Thanks for tuning into this episode of Exit Plan!

Tommy Vincent is a dynamic entrepreneur with a rich background in sales, technology, and mental health businesses. Passionate about finance, his latest venture, Hub Analytics, focuses on automating repetitive accounting tasks and enhancing financial management for small businesses.

By prioritizing customer feedback and maintaining a lean approach, Tommy aims to guide entrepreneurs in exit planning and achieving their financial goals. His journey from successful exits to innovative startups underscores the high-risk, high-reward nature of entrepreneurship, inspiring others with his commitment to long-term success.

Key themes included:

1. Customer-Centric Approach

2. Entrepreneurship Journey and Insights

3. Financial Reporting and Accuracy

4. Importance of Strong Networks

5. Long-term Success Planning

6. Automating Accounting Tasks with AI

7. Exit Planning and Succession

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Website: https://hub-analytics.com/

Email: tommy.vincent@hub-analytics.com

LinkedIn: https://www.linkedin.com/company/hub-analytics-software/?viewAsMember=true

Facebook: https://www.facebook.com/profile.php?id=61554597001535

Instagram: https://www.instagram.com/hub.analytics/

—

Follow Dana on LinkedIn: https://www.linkedin.com/in/danabrobinson/

Follow Dana on Instagram: https://www.instagram.com/danarobinsonofficial/

Subscribe to Dana’s weekly newsletter at https://www.danarobinson.com

—

If the information in these conversations and interviews have helped you in your business journey, please subscribe to the show, and leave me an honest review.

Your reviews and feedback will not only help me continue to deliver great, helpful content, but it will also help me reach even more amazing entrepreneurs just like you!

*Some of these links might be affiliate links. Thank you in advance if you choose to work with one of the companies I believe in. The money I make from your purchase helps to keep the content you enjoy, and rely on to grow your own business, free to you.

Thanks for tuning into this episode of Exit Plan!

Key themes included:

1. Business Lifecycle Understanding in SaaS

2. Financial Literacy in M&A

3. Small to Large Acquisition Journey

4. Importance of CPA in Acquisitions

5. Challenges in Accounting Reconciliation

6. Seller-Buyer Relationship Importance

7. Diverse Team for Scaling Businesses

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Website: www.michaelfrew.com/

Email: podcast@michaelfrew.net

LinkedIn: https://www.linkedin.com/in/michaelfrew/

YouTube: https://www.youtube.com/@michaelfrew

X: https://twitter.com/point_of_frew

Instagram: https://www.instagram.com/point_of_frew/

—

Follow Dana on LinkedIn: https://www.linkedin.com/in/danabrobinson/

Follow Dana on Instagram: https://www.instagram.com/danarobinsonofficial/

Subscribe to Dana’s weekly newsletter at https://www.danarobinson.com

—

If the information in these conversations and interviews have helped you in your business journey, please subscribe to the show, and leave me an honest review.

Your reviews and feedback will not only help me continue to deliver great, helpful content, but it will also help me reach even more amazing entrepreneurs just like you!

*Some of these links might be affiliate links. Thank you in advance if you choose to work with one of the companies I believe in. The money I make from your purchase helps to keep the content you enjoy, and rely on to grow your own business, free to you.

Thanks for tuning into this episode of Exit Plan!

Key themes included:

1. Articulating customer value and pricing.

2. Solving customer problems effectively.

3. Value table exercise components.

4. Price segmentation and strategies.

5. Market segmentation understanding.

6. Raising prices with confidence.

7. "Will I" decision importance.

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Website: www.impactpricing.com/

Email: mark@impactpricing.com/

LinkedIn: https://www.linkedin.com/in/stiving/

YouTube: https://www.youtube.com/channel/UCKnZPFHa_GIDSKlHv_jdYgQ

Podcast: https://podcasts.apple.com/us/podcast/impact-pricing/id1449435549

Blog: https://impactpricing.com/blog/

—

Follow Dana on LinkedIn: https://www.linkedin.com/in/danabrobinson/

Follow Dana on Instagram: https://www.instagram.com/danarobinsonofficial/

Subscribe to Dana’s weekly newsletter at https://www.danarobinson.com

—

If the information in these conversations and interviews have helped you in your business journey, please subscribe to the show, and leave me an honest review.

Your reviews and feedback will not only help me continue to deliver great, helpful content, but it will also help me reach even more amazing entrepreneurs just like you!

*Some of these links might be affiliate links. Thank you in advance if you choose to work with one of the companies I believe in. The money I make from your purchase helps to keep the content you enjoy, and rely on to grow your own business, free to you.

Thanks for tuning into this episode of Exit Plan!