From High school to High 6 Figures in under a year with Joshua | Tyler & Rafael Cortez.
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From High school to High 6 Figures in under a year with Joshua | Tyler & Rafael Cortez.
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From High School → High 6 Figures (in under a year!)
Rafael sits down with Joshua Douchee & Tyler Williams of Silverstone Capital (Chicago) to unpack how they went from a senior-year bathroom cold call to consistent deals and high 6 figures—fast.
We cover:
1️⃣ Scrappy start: JV’ing “dead leads” and early novations that worked in overlooked markets
2️⃣ Role clarity that unlocked scale: ops vs. relationships
3️⃣ Pipeline speed: being the “squeaky wheel” with title/agents to shorten cash conversion cycles
4️⃣ Hard lessons: setting boundaries on nightmare deals vs. doubling down on winners
5️⃣ Wins: a $63k+ spread and why bigger deals are often simpler.
Key takeaway: Solve ugly problems, finish the job, and run a disciplined cadence—conversations close, broadcasts don’t.
Timestamps / Chapters:
00:00 – Intro & who Joshua and Tyler are
02:00 – High school → high 6 figures: the origin story
05:00 – The “bathroom cold call” & first JV wins
09:00 – Novations 101: when and where they work
12:30 – Building buyer lists from real transactions
16:00 – Phone-first cadence (double dial → VM → text)
19:00 – Role clarity that unlocked scale (ops vs relationships)
22:30 – Systems: CRM, cadences, daily huddles
26:00 – Pipeline speed: “squeaky wheel” with title/agents
30:00 – Deal breakdown: the ~$63k spread (why it was simple)
34:00 – Quality control: walking from bad deals, doubling down on winners
38:00 – Hiring ahead of growth & avoiding mis-hires
42:00 – 2025 reality: spreads, soft costs, what’s working
46:00 – Action playbook: what to execute next 30 days
50:00 – Rapid-fire: tools, scripts, KPIs
58:00 – Resources, where to connect & wrap
Connect with Joshua Douchee & Tyler Williams:
Joshua Douchee IG: https://www.instagram.com/joshua.jmd.dochee/
Tyler Williams IG: https://www.instagram.com/tyler.williams_._/
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#Wholesaling #RealEstateInvesting #Novations #Dispositions #Acquisitions #ColdCalling #RealEstatePodcast #EntrepreneurMindset #RafaelCortez #SilverstoneCapital #ChicagoREI #HighSchoolToSixFigures