Rich Blecher
Retired Military officer with experience in AI/ML metadata creation and problem solving
Location
Yorktown, Virginia, US
Company
Try Style LLC
Industry
Fashion
Top Skills
Rich Blecher
Retired Military officer with experience in AI/ML metadata creation and problem solving
Location
Yorktown, Virginia, US
Company
Try Style LLC
Industry
Fashion
Top Skills
Top Skills
AI for Visual Fit
Virtual Tryon has been a technology problem for 15 years. It hasn’t worked well at scale because of inaccurate rendering, processing costs. These conditions have changed in the past 18 months. AI rending quality crossed the commercial threshold and retailers have been struggling with growing returns. We are already in our first enterprise pilot.
Family Values
Highly values family and personal relationships, considering them the ultimate measure of success.
Military Service
Served 20 years in the U.S. Air Force as a navigator and strategist, including 39 deployments.
About Rich
Bio
Rich Blecher’s story starts far from boardrooms and startups.
He grows up in a blue-collar family where money stays tight and work starts early. If the lawn needs mowing or a neighbor needs a ditch dug, he’s already there, hands blistered, earning enough to help buy milk or something better than canned meat for lunch. From the beginning, work isn’t optional—it’s how you take care of people.
He becomes the first in his family to attend college, driven by a single goal: serve and fly.
In 1989, Rich commissions into the U.S. Air Force as a navigator in reconnaissance aircraft. Over the next 20 years, he deploys 39 times. The focus is never medals or recognition—just the mission and doing it better than the day before. Awards collect quietly in a shoebox while he keeps moving forward.
Later, his career shifts from the cockpit to strategy. At the Pentagon and Headquarters levels, he becomes a trusted problem solver, supporting senior leaders, including the Chief of Staff of the Air Force, and contributing to initiatives tied to presidential directives. Along the way, he gains early exposure to artificial intelligence and advanced surveillance systems, helping integrate emerging AI and machine learning into real-world defense programs and training simulations.
After retiring, he carries that same mindset into the private sector—practical, mission-focused, and systems-driven.
When he notices how outdated sizing, guesswork, and returns plague the fashion industry, he sees a familiar problem: a broken feedback loop. Instead of chasing trends, he builds a solution. He founds TryStyle to apply AI to both visual and physical fit—helping shoppers see themselves in clothing while giving designers real-world body data to create better products from the start.
Today, Rich brings together decades of leadership, operational discipline, and applied AI experience to build technology that solves everyday problems at scale.
Above all, he remains grounded by what matters most: 38 years of marriage, three children, and eight grandchildren—the real measure of success.
Company
Try Style LLC
Elevator Pitch
TriStyle is AI-powered visual commerce infrastructure for fashion retail — it lets online shoppers see how clothing will look on their body before they buy. Processing costs dropped from 50 cents to near a penny per render in eight months, which is what makes the unit economics work for the first time at scale. Our first enterprise pilot is with 24-7 Comfort Apparel — existing national distribution through Walmart, Target, Macy's, JCPenney, and Kohl's — and it's structured with a channel partnership clause that turns pilot success into a direct path through 24-7's retailer relationships. We're raising on a $4 million cap via SAFEs.
Industry
Fashion
Website
Team Size
1-5 employees
Funding Stage
Pre-Seed
Funding Raised
None/Bootstrapped
Annual Revenue
$0 to $100k
Skills
| Skill | Strength | Explanation |
|---|---|---|
| AI for Visual Fit | Virtual Tryon has been a technology problem for 15 years. It hasn’t worked well at scale because of inaccurate rendering, processing costs. These conditions have changed in the past 18 months. AI rending quality crossed the commercial threshold and retailers have been struggling with growing returns. We are already in our first enterprise pilot. | |
| Family Values | Highly values family and personal relationships, considering them the ultimate measure of success. | |
| Military Service | Served 20 years in the U.S. Air Force as a navigator and strategist, including 39 deployments. | |
| Military Operations | Executed numerous military operations as a navigator in reconnaissance aircraft during 39 deployments. | |
| Military/Defense Industry | Gained over two decades of experience in military and defense operations and strategic planning. | |
| Leadership | Possesses extensive leadership experience from military service and strategic roles. | |
| Problem Solving | Consistently identified and resolved complex problems at strategic and operational levels. | |
| AI Integration | Successfully integrated AI and ML into complex defense and commercial systems. | |
| Product Management | Managed the development of technology solutions from conception to implementation, focusing on user needs. | |
| Founder | Founded TryStyle to address issues in the fashion industry with an AI-powered solution. | |
| Returns Reduction Strategy | Implemented strategies and technology to reduce product returns in the fashion industry. | |
| Body Data Analysis | Leveraged real-world body data to inform product design and improve fit. | |
| E-commerce Industry | Developed solutions specifically for the e-commerce sector within fashion retail. | |
| Bootstrapping | Successfully launched a company through self-funding. |
Experiences
EDUCATIONHigher Education Institution
Title
College Student
Position Description
Attended college as the first in his family, driven by the goal to serve and fly, which led to commissioning into the U.S. Air Force.
Accomplishment Notes
Became the first in his family to attend college, successfully completing his studies prior to commissioning into the U.S. Air Force.
JOBU.S. Air Force
Title
Navigator & Strategic Problem Solver
Position Description
As a military officer, I spent my career solving problems where being wrong was not an option - including 4-star and Presidential level work at the Pentagon on challenges with no precedent. That experience taught me to identify structural problems clearly, build the right team around the problem, create a solution, then execute without the luxury of iteration. As a real estate investor, I spent 20 years closing institutional capital transactions. I know how investors underwrite risk. I know deals happen through relationships, not pitch decks. I know what the other side of the table is actually thinking. I did not come to TrySTyle as a fashion insider. I came as someone who recognized a structural problem that Technology had finally made solvable - and who knew exactly what team to build around it.
Accomplishment Notes
Successfully completed 39 deployments as a navigator; transitioned to a trusted problem solver, supporting senior leaders including the Chief of Staff of the Air Force; gained early exposure to and integrated AI/ML into real-world defense programs and training simulations. I've bought and sold over 40 residential and commercial properties and have created workbooks to teach others my advanced techniques on investing in real estate.
JOBTry Style LLC
Title
Founder
Position Description
Virtual Tryon has been a technology problem for 15 years. It hasn’t worked well at scale because of inaccurate rendering, processing costs. These conditions have changed in the past 18 months. AI rending quality crossed the commercial threshold and retailers have been struggling with growing returns. We are already in our first enterprise pilot. Technology over the past year has changed the tryon processing costs from $1-$0.50/render or more to nearly a penny. Major retailers processed over $400B in returns last year and the cost per return is climbing. The incumbent solution is to tell the customer to keep the item. That’s not a strategy. That’s a problem that’s gotten expensive enough that someone had to solve it.
Accomplishment Notes
TryStyle’s first enterprise pilot is with 24/7 Comfort Apparel, a Los Angeles–based women’s apparel company with broad retail distribution through channels including Amazon, Walmart, JCPenney, Kohl’s, Macy’s and Target. The pilot began July 2026 and runs for 60 days, testing approximately 30–50 SKUs with clear with the goal of moving into a paid SaaS subscription and expanding across additional products. Beyond the pilot, TryStyle is also structuring a partnership with 24/7 to promote TryStyle through their existing distribution channels.
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