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Tim Milazzo

Tim Milazzo

Revenue ops & product marketing consultant; ex-StackSource CEO

timmilazzo
New Smyrna Beach, Florida
Joined February 2025

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Summary

Founder and operator with deep product/market experience in proptech and commercial real‑estate finance. He co‑founded StackSource to simplify CRE lending by matching borrowers to lenders and building tools (browser extension, APIs) that automated parts of the origination workflow; under his leadership the company grew rapidly and received coverage and fundraising attention before a 2024 merger/transition. stacksource+3
Background in revenue, sales operations, and analytics from large tech platforms (Google, LiveRail, Facebook) that shaped his operational approach—combining data, tooling, and sales process design—later applied to scaling StackSource and now to fractional/revenue operations consulting. kingscrowd+2
Transitioned from founder to advisor/consultant after StackSource's exit—packaging lessons learned (growth, fundraising, product-market fit, and cultural/operational pitfalls) into Salt & Wisdom to help early founders avoid common scaling mistakes. saltandwisdom+1
Hands-on experimenter and community-minded entrepreneur: runs a local sustainability-minded side project (Ugly Beer) to test circular-economy ideas in public markets, demonstrating a bias for rapid MVP testing and storytelling to validate product and community fit. medium+1
Personal life and values: positions business as a form of ministry and emphasizes family and community in public bios; based in a Florida beach town and active in local initiatives and nonprofit advisory. saltandwisdom+1

Work

Education

Projects

Writing

Testing the waters — ugly bottles

October 1, 2023

First-person writeup of the Ugly Beer pilot: problem framing (regional glass recycling limits), MVP decision to brew root beer, pilot sales results, unit economics, and learnings for scaling a bottle‑reuse idea.

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Introducing StackSource

August 1, 2016

Overview of the StackSource platform at launch, explaining product goals: streamlining loan prep materials and connecting borrowers with lenders via a modern online platform.

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How (Not) to Launch a Startup

November 1, 2024

Lessons on focus and product-market fit: choosing a narrow, crush-worthy problem rather than broad coverage to unlock sustainable growth.

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How (not) to find your marketing groove

November 1, 2024

Practical advice on shifting from feature-focused messaging to benefit-driven marketing and collecting objective feedback from users.

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7 ways I avoided founder-led sales, and which ones (didn't) work

January 1, 2025

First-person reflection on founder-led sales, common avoidance tactics, and steps founders can take to get back into the sales seat.

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7 things you should know about a potential co-founder

April 1, 2025

A practical framework and specific questions to evaluate fit, capabilities, and alignment when deciding on a co-founder or business partner.

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Beyond the Scorecard: The Story You Own Shapes Your Leadership

February 1, 2025

On ownership, personal responsibility, and how leaders should focus on internal benchmarks rather than external excuses.

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The Skip Button Is a Trap

November 1, 2025

An essay warning against shortcuts and the impulse to 'skip' hard work—argues for embracing difficulty and bounded downside experiments.

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Princess Ride or Die

September 1, 2025

A personal narrative about balancing family priorities with startup life and the value of small, meaningful choices during the grind.

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Hobbies

Brewing / Ugly Beer project and interest in circular‑economy experiments (re‑using glass bottles); participates in local farmer's markets and community experiments. medium+1

Writing (Medium posts, blog posts) and podcast/interview appearances on proptech and CRE topics. stacksource+1