Podcast Summary

Podcast Title: The Science of Flipping
Episode: From Oil & Gas to 200+ Deals a Year, and Dominating TV Ads | Luke Winter
Host: Justin Colby
Guest: Luke Winter
Date: August 29, 2025

Overview

This episode features a deep-dive conversation between host Justin Colby and guest Luke Winter, a former oil & gas executive turned prolific real estate investor and marketing strategist. Luke shares his journey from the corporate world to scaling a real estate business to 200+ deals per year and discusses how he now helps other investors dominate their markets using data-driven TV advertising through his company, Hello Pro. The episode is rich with practical advice on entrepreneurship, executing marketing at scale, and the mindset needed to succeed in today's tougher real estate market.

Key Discussion Points & Insights

1. From Corporate Oil & Gas to Real Estate Entrepreneurship

• Luke’s Decision to Leave Corporate (01:44–05:58)
  • Climbed ranks in oil & gas, reaching the "high water mark."
  • Lack of fulfillment and the birth of his daughter sparked self-reflection.
  • Desired a life of meaningful stories, leadership, and risk-taking.
  • Chose to leave corporate for full-time real estate investing.
  • Quote:
    “I wanted a lot more of life. I wanted really to look up to the people that are in my network. ... Prove to myself also that I can do more. I was built for more.” — Luke Winter (05:16)

2. Mindset & Self-Actualization: The Fuel for High Performance

• Chasing Growth and Meaning (06:29–07:57)

  • Justin and Luke discuss the “chip on your shoulder” and intrinsic drive.
  • The importance of believing you are built for more and seeking fulfillment.
  • Luke introduces the "human action model," requiring:
    1. A vision of a better state.
    2. A sense of unease with the current state.
    3. A belief you can get there.

• The Role of Community and Masterminds (08:05–11:07)

  • Both emphasize the power and ROI of paying for access to networks and mentorship.
  • Community builds both business development and mindset.
  • Quote:
    “There’s not a lot of shortcuts in business, but [masterminds] are one. Just get straight to the people who have the answers, who have been through what you are trying to do.” — Luke Winter (11:07)

3. Scaling a High-Volume Real Estate Business

• Operational Excellence (15:10–19:15)
  • Luke recounts scaling a “messy” business from 40–50 to 200+ deals annually.
  • Focused on streamlining operations, dialing in recruiting, and implementing data-driven marketing.
  • Negotiated equity upon joining the real estate company, eventually leading to a successful exit.
  • Notable Moment:
    Justin points out that actually exiting a flipping/wholesaling business as intended and documented is "very unique and a feather in your cap" (18:48).

4. TV Advertising for Real Estate Investors

• Transition to Marketing & Hello Pro (19:16–22:00)

  • After his exit, Luke sought to innovate in investor marketing.
  • TV advertising was core to his own investing success, due to its scale and quality of leads.
  • Outlines differences between brute force cold calling and efficient TV lead gen.
  • As TV spend goes up, stations provide more value, ad placements, and higher efficiency—unlike list-based cold outreach.

• Ideal Clients for TV Ads (23:13–24:12)

  • Best for investors closing 2–3+ deals/month, with an established consumer-facing brand and a converting website.
  • TV advertising has a higher cost-per-lead, but delivers higher quality, more profitable leads.
  • Beginners should use cheaper channels before adding TV for scale.

• Practical TV Ad Strategies (25:48–27:19)

  • Minimum budgets: $5,000/month in smaller markets; larger for metro areas.
  • Frequency (multiple spots per week/day) is critical; daily exposure in same time slots builds recall.

• The Importance of Branding and Consumer-facing Business (27:19–29:39)

  • A memorable, unified brand is vital—cannot run a scalable “hustle” with generic names.
  • Consistency across web, TV, and print builds trust and conversion.

• Website, CRM, and Lead Conversion (30:04–33:31)

  • Many clients come unprepared: non-converting websites, poor forms, lack of after-hours response.
  • Half of TV leads will check your website before reaching out.
  • Luke consults clients on web and lead flow best practices.

• Follow-Up, Nurture, and Accountability (32:44–34:26)

  • TV leads require strong CRM, follow-up, and automation.
  • Luke meets monthly with clients to coach and suggest improvements.
  • Quote:
    “I'm only going to keep you as a client as good as you are at converting these leads, so if you suck, you're going to leave me. And it's not because I'm not doing my job, it's because you can't convert the leads I'm giving you.” — Justin Colby (32:28)

5. Success Requires Relentless Ownership

• Entrepreneurial Realities (35:43–40:57)
  • Many investors fail by working only “business hours” and not answering leads after hours.
  • Owners must be prepared for “24/7, 365” mentality at least in early years.
  • Justin: “Entrepreneurs need to wake the up. It is a hundred percent, seven days a week, 24, seven, all on your shoulders until the point of scale.” (36:00–37:12)
  • Technical tips: Use live answering services (Call Porter, Answer Connect, etc.), call routing for after hours.
  • Plugging marketing dollars into a leaky conversion process is wasted money.
  • Most people blame the marketing, not their own systems.
  • Quote:
    “You got a leaky bucket. You're pouring more water into a leaky bucket. And they're gonna blame the marketing company.” — Justin Colby (38:26)

6. State of the Market: Tough Times, More Opportunity

• Winners Double Down, Losers Wash Out (38:49–42:03)
  • Only dialed-in operators thrive during hard markets; marginal players are being washed out.
  • Now is the time to double down, take market share, and be remembered when the dust settles.
  • Wholesale is much harder than during “unicorn” COVID years; the industry is weeding out the uncommitted.
  • Focus now is on higher-margin, lower-volume business over “chasing deals.”
  • Quote:
    “It is massive opportunity if you know what you're doing. Massive opportunity to take market share, because the average players are getting washed out.” — Luke Winter (38:49)

Notable Quotes & Memorable Moments

• “I wanted the war stories. I wanted the trials and tribulations. I wanted the successes.” — Luke Winter on why he left corporate for entrepreneurship (04:13)
• “A vision of a better state, a sense of unease, and a belief you can get there”—the three prerequisites for making real change, according to Luke. (07:35)
• “It’s a shortcut. There’s not a lot of shortcuts in business or life, but that is one of them.” — Luke Winter on masterminds (11:07)
• “Direct mail, PPC, TV—if you have a few of those as your foundation, the world is your oyster.” — Luke Winter, on scalable marketing (25:34)
• “Frequency is very important… If you air one ad a month, nobody will remember you.” — Luke Winter (26:49)
• “You're building a consumer facing business, not a hustle. Invest time and energy so your brand looks and feels the same everywhere.” — Luke Winter (29:20)
• “Entrepreneurs need to wake the up. It is a hundred percent, seven days a week, 24, seven, all on your shoulders until the point of scale.” — Justin Colby (36:00–37:12)
• “You got a leaky bucket. You're pouring more water into a leaky bucket.” — Luke Winter (38:26)
• “You take market share, you go deeper when everyone’s running out… because you’re able to eat up that market share now.” — Justin Colby (39:13)
• “Only the best of the best operators… are spending their way there.” — Justin Colby, on today’s wholesale business (41:29)

Timestamps for Key Segments

• Luke’s Journey Out of Corporate/Oil & Gas: 01:44–07:57
• Entrepreneurial Mindset & Masterminds: 06:29–11:22
• Scaling a High-Volume REI Business: 15:10–19:15
• TV as a Marketing Channel: 19:16–27:19
• Brand Building & Consumer Focus: 27:19–29:39
• Web, CRM, and Lead Conversion Essentials: 30:04–34:26
• After-Hours & Team/Process Failures: 34:26–38:29
• Market Cycles, Opportunity for Operators: 38:49–42:03

Conclusion

Luke Winter’s story showcases the challenging but rewarding leap from a secure, well-paying corporate life to entrepreneurial risk and growth in real estate. Through his perspective as both a high-velocity investor and marketing strategist, listeners gain a transparent look at what it takes—mindset, systems, brands, smart marketing, and pure hustle—to succeed in today’s real estate industry. Both Luke and Justin stress that in the current market, only the most committed, systemized operators will thrive, and that trusting in and investing into the right voices, networks, and scalable marketing (like TV ads) is more critical than ever.

For more on Luke Winter and his TV ad services, visit: thehellopro.com (41:58)

If you’re a growth-focused investor wanting a scalable edge or more fulfillment, this episode delivers both inspiration and tactical insight.