FOUNDERS IN THE TRENCHES
Founders know their business better than anyone. Coaching works best when it amplifies their strengths through sharp questions, A/B decisions, and stopping to appreciate breakthroughs. Focus areas include loss leader strategy, early customer self funding, team alignment, and strategic planning.
This is not coaching from the sidelines. I have multiple past wins, and I am in the trenches right now. Coaching is part of the craft of entrepreneurship, not a side identity. Guidance should be usable, applied, and tested in real work. The founders I coach teach me too.
Get on my coaching calendar: meet.flik.com
T.J. Muro, Founder & CEO
“I reached out to Donato while navigating some real challenges as a solo founder, looking for perspective and clarity as I worked through a complex situation. What stood out immediately was how quickly he understood the context and helped me cut through the noise.
Donato had a way of asking the right questions and reframing problems so they felt manageable and actionable. Rather than jumping to solutions, he helped me step back, align my thinking, and focus on what actually mattered at that moment. That kind of clarity was incredibly valuable when building on my own and trying to make the right decisions under pressure.
Our conversations were thoughtful, practical, and grounded in real experience. He offered honest insight without ego or agenda, which made his guidance especially impactful.
If you’re a founder navigating uncertainty and looking for clear, experienced perspective, Donato genuinely helped me get unstuck and move forward with confidence.”
Leading the transformation of digital advertising and GTM strategies with DatAI-Driven MarkITing Innovation Solutions.
- Privacy-first ad platform
- Uses CRM data—not cookies—to eliminate fraud
- Delivers 35% higher ROAS while staying fully compliant with GDPR, CCPA, and HIPAA.
Michael Esser, Founder & CEO
“What is life but a series of hobbies and passions, Donato brings that passion to every project he chooses to coach. It’s having a truly battle-tested, nine-figure–exit advocate in your corner.
He’s been around the block enough times to tell you which shortcuts not to take, where founders consistently misjudge risk, and how technical, architectural, and VC realities actually collide in the real world. His feedback spans product look and feel, technical architecture, founder decision-making, investor dynamics, and the unwritten rules that never show up in pitch decks.
What I appreciate most is that Donato doesn’t posture. He listens closely, pressure-tests assumptions, shares hard-earned stories from experience, and helps you avoid expensive mistakes before they happen. Whether you’re a technical or non-technical founder navigating growth, his perspective is practical, candid, and grounding.
As the force behind FireThief, DataZ, Flik, and a growing portfolio of emerging companies on the path toward a second major exit, Donato brings real operating experience, not theory, to the table.
An avid entrepreneur, an enthusiastic businessman, and a straight shooter, Donato adds real signal in a space full of noise. I highly recommend working with him if you want insight rooted in experience, not hype.”
Close.win helps sales teams book qualified, scheduled, and showed meetings — automatically.
- Replaces cold calling with intelligent outreach that connects your reps directly to buyers.
- Uses voice, email, and SMS automation with deep compliance and analytics.
- Suitable for SaaS sales team or a nationwide calling operation.
Ed Jalinske, Founder & CEO
“I’ve had the pleasure of working with Donato Diorio and can say without hesitation that he is a thoughtful, disciplined, and exceptionally insightful investor and advisor.
Donato has a rare ability to quickly understand complex businesses, particularly in technology and cybersecurity, and ask the right questions. His feedback consistently cuts through noise and focuses on what truly matters: fundamentals, scalability, execution, and long-term value creation. He brings both strategic rigor and real-world operating experience to every conversation.
What I value most about Donato is his integrity and founder-first mindset. He is candid, constructive, and genuinely invested in helping companies succeed, not just in making a deal. His perspective is grounded, his advice is actionable, and his professionalism sets a high bar.
In fact, when I first met Donato at Founder’s Fest in Milwaukee, I had three actionable takeaways after one casual conversation with him, namely, in the context of introducing your business to somebody for the first time, Donato’s guidance: 1. What’s the problem you’re trying to solve? 2. What are you doing to address the problem (technology solution or otherwise)? 3. How are you unique? Those three focused pillars set the tone for our Paxie.ai MVP development.
Any founder, executive team, or organization would be fortunate to work with Donato. I highly recommend him as an investor, advisor, and strategic partner. “
A full-purpose cybersecurity technology and services firm simplifying cybersecurity tech and making the industry more accessible, while also improving the cyber maturity of people, organizations, and enterprises worldwide.
- Cybersecurity Technology & Services
- Cyber Education, Training, and Awareness
- Cybersecurity Talent Recruitment & Career Services
