Ep. 102 | Serial Entrepreneurship with Robert Oglesby | SuccessFlow Podcast episode artwork

EPISODE · May 28, 2025 · 50 MIN

Ep. 102 | Serial Entrepreneurship with Robert Oglesby | SuccessFlow Podcast

from SuccessFlow Podcast · host Phil Crawford and Steven Harris

In this episode of the Success Flow podcast, Phil Crawford and Steven Harris sit down with Robert Oglesby, an experienced entrepreneur in the appraisal industry. Robert shares his journey from the restaurant business to founding his own appraisal company, discussing the challenges and misconceptions surrounding appraisals, the impact of market trends, and the lessons learned during the 2008 financial crisis. He also delves into the complexities of managing a growing business, the importance of compliance and licensing, and the value of personal development and networking through groups like Junto. In this conversation, Robert Oglesby shares his insights on continuous learning, navigating life after a business exit, and the challenges of entrepreneurship. He emphasizes the importance of mental health, fitness, and having independent advisors during significant life transitions. Oglesby also discusses his current ventures and the definition of success, highlighting the balance between personal fulfillment and professional achievements.To connect with Steven and ways he can help:Speaking Engagements/Team Workshops ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: https://oppoflow.com/speaking-engagements⁠Founder/Creator : https://oppoflow.com/Co-Owner of Journey Payroll PHX : https://www.journeypayrollhr.com/Subscribe via Email : https://oppoflowstorybook.beehiiv.com/Actionable Playbooks : https://oppoflow.com/playbooksConnect everywhere else https://linktr.ee/steven.oppoflowTo connect with Phil and contact directly:https://phillipcrawford.com/https://twitter.com/PhillipCrawfordhttps://www.instagram.com/flowstatecrawford/https://www.linkedin.com/in/phillip-crawford-92a84115/

In this episode of the Success Flow podcast, Phil Crawford and Steven Harris sit down with Robert Oglesby, an experienced entrepreneur in the appraisal industry. Robert shares his journey from the restaurant business to founding his own appraisal company, discussing the challenges and misconceptions surrounding appraisals, the impact of market trends, and the lessons learned during the 2008 financial crisis. He also delves into the complexities of managing a growing business, the importance of compliance and licensing, and the value of personal development and networking through groups like Junto. In this conversation, Robert Oglesby shares his insights on continuous learning, navigating life after a business exit, and the challenges of entrepreneurship. He emphasizes the importance of mental health, fitness, and having independent advisors during significant life transitions. Oglesby also discusses his current ventures and the definition of success, highlighting the balance between personal fulfillment and professional achievements.To connect with Steven and ways he can help:Speaking Engagements/Team Workshops ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: https://oppoflow.com/speaking-engagements⁠Founder/Creator : https://oppoflow.com/Co-Owner of Journey Payroll PHX : https://www.journeypayrollhr.com/Subscribe via Email : https://oppoflowstorybook.beehiiv.com/Actionable Playbooks : https://oppoflow.com/playbooksConnect everywhere else https://linktr.ee/steven.oppoflowTo connect with Phil and contact directly:https://phillipcrawford.com/https://twitter.com/PhillipCrawfordhttps://www.instagram.com/flowstatecrawford/https://www.linkedin.com/in/phillip-crawford-92a84115/

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Ep. 102 | Serial Entrepreneurship with Robert Oglesby | SuccessFlow Podcast

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This episode was published on May 28, 2025.

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In this episode of the Success Flow podcast, Phil Crawford and Steven Harris sit down with Robert Oglesby, an experienced entrepreneur in the appraisal industry. Robert shares his journey from the restaurant business to founding his own appraisal...

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