ABOUT ICON
Built by Operators, for Operators
Nashville-based AI consulting and M&A advisory firm for lower middle market business owners. Operators who advise. Founded by Daniel Askew, with $450M+ in sales across his 25-year operating career.
Our Story
Most M&A firms are built by bankers. Career deal processors who have never made a payroll, never lost sleep over a customer who threatened to leave, never sat in a room wondering whether there was enough cash to cover Friday. They are good at the mechanics of transactions. They have never built anything.
Icon was built by someone who has. Daniel Askew spent 25 years building companies from scratch before he ever advised on a deal, with $450M+ in sales across that operating career. He raised capital, negotiated acquisitions, and made expensive mistakes with his own money. By the time he founded Icon, he had been the owner sitting across the table from an advisor with impressive credentials and no idea what it cost to build what was being sold.
Rachel Askew joined as COO and Operating Partner in 2025, bringing 25+ years of leadership across healthcare, financial services, and technology. She built the systems, structure, and delivery that turned Icon from a founder-led practice into a firm. Together, they built the firm they wished they had as owners: operators who advise.
What Makes Icon Different
Operator Credibility
Your advisor has built companies, negotiated exits, raised capital, and made payroll. Not theoretically. With his own money, his own risk, his own sleepless nights. That changes how we advise because we know what you are protecting. We have been in your chair.
Our Own AI System
We run Icon on our own AI system. It helps us source deals, track the market, build valuation analysis, and turn around client materials quickly. It lets a small team cover a lot of ground.
Real Relationships
We know private equity firms, family offices, strategic buyers, and business owners across the Southeast and nationally. We put those relationships to work on your deal.
Co-Entrepreneur Model
Daniel does not just advise business owners. He actively co-founds and operates businesses alongside them. This is not a side hobby. It is how we stay sharp. When your advisor is also an active operator, the advice is grounded in reality, not theory. We eat our own cooking.
One Team, Every Stage
We built Icon to work with owners at every stage: putting AI to work, exit planning, valuation, selling, buying, raising capital, fractional leadership, and commercial real estate. One relationship. Every stage.
Relationships First
We take on a limited number of engagements so every client gets our full attention. We measure success by outcomes and referrals. The best compliment we receive is when a business owner tells another business owner: “Call Daniel.”
How We Serve Business Owners
Six services, one team. Start with the one you need today.
Icon AI
AI that does real work inside your business. We find where AI pays off, put it to work across your core workflows, and train your team to run it. You own everything we build.
Icon Exit
Sell your business on your terms, when you’re ready. Confidential sell-side M&A from operators who have sat in your chair.
Exit Planning · Business Valuation · Exit Readiness Score · Get your Snapshot: talk to us
Icon Acquire
Find and buy the right business. You tell us what you want to own. We go find it, screen it, make the introductions, and run the deal with you through LOI, diligence and close.
Icon Capital
Raise the money to grow, buy, or buy out a partner. Growth capital, acquisition financing, and recapitalization for real businesses with real revenue.
Icon Partner
Operating leadership inside your business. A fractional COO or CPO who works with your team every week and owns the work.
Icon Commercial
Your business and your building, advised together. Sell them together, sell them separately, or keep the building and lease it back.
Selling a business with real estate · Sale-leaseback advisory
Free tools and a conversation: Get your Snapshot: talk to us, Exit Readiness Score, and more in the Toolkit.
Meet the Team
Daniel Askew
Founder & CEO
Daniel is a Nashville native and serial entrepreneur with 25+ years as an operator. Before founding Icon, he built and led companies from startup through scale.
Over his 25-year operating career, before Icon, Daniel personally drove $450M+ in sales at the companies he built and led. Daniel still co-founds and runs businesses alongside owners he advises, because the best advisors still operate. He leads every Icon client engagement personally, and he knows what it is like to be the founder negotiating a deal that represents everything he built.
Before Icon, Daniel was a partner at Five Doors Network, where he built the company’s Southeast region. Five Doors ranked No. 113 on the 2018 Inc. 500 list of America’s fastest-growing private companies.
Rachel Askew
COO & Operating Partner
Rachel brings 25+ years of leadership across healthcare, financial services, and technology. She builds teams, fixes operations, and puts in the systems that let a growing company scale without losing its culture.
At Icon, Rachel runs client delivery, systems, team operations, and the technology behind the firm. If Daniel is the vision and energy, Rachel is the precision and execution.
Nashville Roots, National Reach
Icon is headquartered in Nashville, Tennessee, and works with owners across the Southeast and nationally. Our market pages cover Nashville, Memphis, Clarksville, Bowling Green, Birmingham, Huntsville, Knoxville, Atlanta, and Chattanooga.