CRE Broker Playbook with Jake Crandall

Hosted by Jake Crandall

Business Entrepreneurship

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May 2026

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About the show

What actually makes a great commercial real estate broker? That's the question Jake Crandall is on a mission to answer. Every week he sits down with the sharpest brokers, marketers, and allied professionals in the business to find out what's working, what's not, and what it really takes to build a career worth having in CRE. Whether you're closing your first deal or your hundredth, there's a play in here for you.

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19 recent

May 1, 202622 min

How Ken Ashley Survived 2009 and Rebuilt for Volatile Cash Flow

Ken Ashley has spent nearly 30 years at Cushman & Wakefield Atlanta, but the conversation that shaped his career happened over breakfast in the mid-90s. In this episode, Ken shares how that breakfast pulled him out of a CFO role and into commercial real estate, and why he's spent the rest of his career trying to repay it.We dig into the 2009 downturn, when his wife Karen sat him down in tears and told him they were in trouble. Ken walks through the two paths in front of him, the one he chose, and the permanent changes he made to his business afterward, including building a roster of 14 enterprise accounts (with a goal of 20) to smooth out lumpy cash flow.We also cover:His marketing thesis after COVID and why the buddy-call model is dyingThe difference between sales and marketing, and how social media earns him the right to ask senior execs for adviceWhy he stayed at a big shop for three decades and what it actually unlocksCREI Summit 2026 in Savannah and the Create Lab content sessionsHis new book, The Prescription, launching March 10thIf you're a CRE broker trying to build a career that survives the next downturn, this one's worth your time.

April 17, 202641 min

How CRE Brokers can Master their CRM

Ian Stroud, a real estate broker in Indiana, discusses the development and implementation of the CRE operating system he created on Notion. The system serves as a comprehensive business management tool, integrating AI, automation, and email functionality. Ian shares insights on using Notion for personal and business purposes, as well as his tech stack and tools. He also explores the use case for brokers and provides feedback on the system's impact.TakeawaysDevelopment of a comprehensive CRE operating system on NotionIntegration of AI, automation, and email functionalityUse of Notion for personal and business purposesInsights on tech stack and toolsUse case for brokers and feedback on the system's impactChapters00:00 Introduction and Background09:13 Development and Implementation of the System16:29 Use of AI and Automation22:12 Use of Notion for Personal and Business Purposes31:10 Use Case for Brokers and Feedback

April 10, 202629 min

Water Cooler Conversation with Carson Baird

The conversation covers the importance of personal branding and authenticity in digital presence, the impact of external factors on business performance, and the significance of networking and relationship building in commercial real estate.TakeawaysPersonal BrandingDigital PresenceChapters00:00 Personal Branding and Authenticity in Digital Presence10:05 Networking and Relationship Building in Commercial Real Estate

April 3, 202646 min

How CRE Brokers can Master Social Media

Fly Jamerson is a social-media strategist and content creator based in Baton Rouge, Louisiana.She helps commercial real estate brokers turn everyday deal stories and field insights into high-impact social media content.The conversation covers topics related to marketing collaboration, content creation, specialization vs. generalization, measuring social media success, content distribution and engagement, analyzing social media performance, social media analytics and business impact, reaching the right audience on social media, and effective content creation and distribution.The discussion emphasizes the importance of a consistent content creation workflow and the impact of social media on business growth. The conversation covers topics related to translating personal voice into text, calibrating AI to personal style, optimizing content production for time, maximizing social media efficiency, Movo Media Marketing's services, investing in personal business, video and podcast content strategy, and contacting Fly Jamerson for further engagement.Chapters* 00:00 Introduction and Marketing Collaboration* 05:59 Specialization vs. Generalization* 13:04 Analyzing Social Media Performance* 18:53 Reaching the Right Audience on Social Media* 25:11 Consistent Content Creation Workflow* 31:27 Calibrating AI to Personal Style* 37:06 Movo Media Marketing's Services* 43:20 Investing in Personal Business* 52:26 Contacting Fly Jamerson

March 27, 202435 min

Entrepreneurship and Family with Anthony Herrera

I interview my former professor Anthony Herrera about his career and various ventures into entrepreneurship. We cover: - is there value in an accounting degree? - how do you go about solving accounting talent shortage? - prioritizing family v business - executive coaching Thank you for joining us!

March 26, 20244 min

CRE-CFO #1: How do you get paid?

If you're a commercial real estate broker and are tired of getting killed by your taxes, then you've come to the right place. You're an entrepreneur, ever since you started getting paid by 1099, you became a business owner. And now it's time to act like one. If you'd like to get in touch with us, please reach out at cre-cfo.com and fill out the form there. We'll be in touch as soon as we can.

February 14, 202428 min

Fort Capital Founder + Executive Chairman, Chris Powers -

Thank you to Chris Powers, Founder + Executive Chairman of Fort Capital for joining me to discuss growing a business through podcasting and social media, transitioning from CEO to Chairman, and prioritizing the other parts of life while heading up the fastest growing private real estate business in Texas. On this episode Chris shares his wisdom, knowledge and expertise in: - Using his podcast and social media presence to grow his business - Transitioning from CEO to Chairman - How he manages to prioritize his personal life while being heavily involved in a successful business Thanks for listening! James “Jake” Crandall offers products and services using the following business names: Foster Financial Group or Canvas Financial – insurance and financial services | Ameritas Investment Company, LLC (AIC), Member FINRA(www.finra.org)/SIPC(www.sipc.org) – securities and investments | Ameritas Advisory Services (AAS) – investment advisory services. AIC and AAS are not affiliated with Foster Financial Group or Canvas Financial. Products and services are limited to residents of states where the representative is registered. This is not an offer of securities in any jurisdiction, nor is it specifically directed to a resident of any jurisdiction. As with any security, request a prospectus from your representative. Read it carefully before you invest or send money. A representative will contact you to provide requested information. Representatives of AIC and AAS do not provide tax or legal advice. Please consult your tax advisor or attorney regarding your situation. Information posted to this site by 3rd parties or links to 3rd party sites are not created or endorsed by AIC, AAS or their representatives. Their information is believed to be from reliable sources; however, their content cannot be guaranteed. All of the endorsements and/or client testimonials posted on this (Facebook/LinkedIn/Twitter page) are unpaid and unsolicited. The experiences and views shared do not necessarily represent the perspectives or experience of all clients. Any review or discussion of individual investments and/or performance or results should not be construed as indicative of the experience of all clients, nor does it offer any assurance or indication of future results.

February 1, 202430 min

Garrett Starks talks about why Insurance has gotten so expensive

Garrett Starks joins to discuss navigating rising insurance costs. Tips were shared for finding the best deals through an independent broker, reviewing coverage needs for various business and property types, and working proactively with brokers to evaluate insurance options in the current challenging market. Enjoy! Find Garrett on Linkedin James “Jake” Crandall offers products and services using the following business names: Foster Financial Group or Canvas Financial – insurance and financial services | Ameritas Investment Company, LLC (AIC), Member FINRA(www.finra.org)/SIPC(www.sipc.org) – securities and investments | Ameritas Advisory Services (AAS) – investment advisory services. AIC and AAS are not affiliated with Foster Financial Group or Canvas Financial. Products and services are limited to residents of states where the representative is registered. This is not an offer of securities in any jurisdiction, nor is it specifically directed to a resident of any jurisdiction. As with any security, request a prospectus from your representative. Read it carefully before you invest or send money. A representative will contact you to provide requested information. Representatives of AIC and AAS do not provide tax or legal advice. Please consult your tax advisor or attorney regarding your situation. Information posted to this site by 3rd parties or links to 3rd party sites are not created or endorsed by AIC, AAS or their representatives. Their information is believed to be from reliable sources; however, their content cannot be guaranteed. All of the endorsements and/or client testimonials posted on this (Facebook/LinkedIn/Twitter page) are unpaid and unsolicited. The experiences and views shared do not necessarily represent the perspectives or experience of all clients. Any review or discussion of individual investments and/or performance or results should not be construed as indicative of the experience of all clients, nor does it offer any assurance or indication of future results.

February 8, 202427 min

Life + Disability Insurance: Do you need it? with Chase Clack

Life insurance should be simple. But its not. If you have children or a spouse that depends on your earnings, come learn about life insurance with me and Chase Clack! James “Jake” Crandall offers products and services using the following business names: Foster Financial Group or Canvas Financial – insurance and financial services | Ameritas Investment Company, LLC (AIC), Member FINRA(www.finra.org)/SIPC(www.sipc.org) – securities and investments | Ameritas Advisory Services (AAS) – investment advisory services. AIC and AAS are not affiliated with Foster Financial Group or Canvas Financial. Products and services are limited to residents of states where the representative is registered. This is not an offer of securities in any jurisdiction, nor is it specifically directed to a resident of any jurisdiction. As with any security, request a prospectus from your representative. Read it carefully before you invest or send money. A representative will contact you to provide requested information. Representatives of AIC and AAS do not provide tax or legal advice. Please consult your tax advisor or attorney regarding your situation. Information posted to this site by 3rd parties or links to 3rd party sites are not created or endorsed by AIC, AAS or their representatives. Their information is believed to be from reliable sources; however, their content cannot be guaranteed. All of the endorsements and/or client testimonials posted on this (Facebook/LinkedIn/Twitter page) are unpaid and unsolicited. The experiences and views shared do not necessarily represent the perspectives or experience of all clients. Any review or discussion of individual investments and/or performance or results should not be construed as indicative of the experience of all clients, nor does it offer any assurance or indication of future results.

April 26, 20243 min

CRE CFO #5: How much cash should a CRE Broker have on hand?

If you're a commercial real estate broker and are tired of getting killed by your taxes, then you've come to the right place. You're an entrepreneur, ever since you started getting paid by 1099, you became a business owner. And now it's time to act like one. If you'd like to get in touch with us, please reach out at ⁠⁠⁠cre-cfo.com⁠⁠⁠ and fill out the form there. We'll be in touch as soon as we can.