About Winding Oaks Consulting – Your Trusted Small Business Partner in Central Texas

Our Start

After years of working in the small-to-mid-size business market, our founder, Matt Quicke, saw a common challenge: passionate business owners often have incredible ideas and drive—but struggle to scale, improve profitability, or manage complex financial and operational demands.

Matt launched Winding Oaks Consulting with a simple mission: to bring the expertise and insights of a seasoned business strategist to small businesses that may not have access to executive-level support.

We believe every business deserves a partner who understands their goals, speaks their language, and helps turn ambition into measurable success. At Winding Oaks, we’re that partner—delivering clarity, strategy, and results to help your business thrive.

Matt Quicke - Founder & CEO

At Winding Oaks Consulting, our mission is to help small businesses thrive by delivering strategic insights, optimized operations, and innovative solutions. We partner with owners to strengthen financial performance, enhance efficiency, and unlock growth—providing the expertise they need to succeed without the overhead of a full-time executive team

We aim to be the trusted partner for small businesses in the Texas Hill Country, empowering them with clarity, strategy, and systems to achieve sustainable growth and long-term success.

Our Mission

Our Vision

Our Approach

At Winding Oaks Consulting, we cut through the noise and focus on what actually moves the needle for your business: measurable improvements in revenue, net income, efficiency, and scalability.

• No fluff, just results — We skip endless meetings, generic templates, and theoretical advice. Every recommendation is practical, prioritized, and tied directly to your bottom line.

• Flexible support that fits your needs — Choose advisory guidance for quick strategic input, fractional leadership for ongoing C-suite perspective, or fully embedded support when you need hands-on execution without hiring full-time.

• C-suite level experience without big-agency prices — You get the same high-level strategic insights and operational know-how that teams pay six figures for—delivered affordably and tailored to small-to-mid-size businesses in the Texas Hill Country.

• We’re here to support you and your vision — Your goals drive everything. We partner closely with business leaders like you—understanding your ambitions, respecting your independence, and providing the clarity, systems, and strategies to turn your vision into sustainable success.

We don’t pretend to have all the answers upfront. We start by listening, then deliver targeted solutions that produce real, trackable progress.

Ready to see what this looks like for your business? Book a free consultation.

Serving Central Texas in the Heart of the Hill Country

We live and work in Boerne, Kendall County—ground zero for one of the fastest-growing areas in Texas. Kendall County continues to rank among the state's top counties for population and economic expansion, with projections showing strong double-digit growth through the late 2020s. This boom brings incredible opportunities: new residents, rising demand for local services, tourism influx, and a thriving small business ecosystem fueled by proximity to San Antonio and the natural appeal of the Texas Hill Country.

We understand the excitement—and the realities. The same growth that creates openings for innovative entrepreneurs also intensifies competition. More businesses are entering the market, from retail and hospitality to professional services, making it harder to stand out, manage cash flow, optimize operations, and scale profitably without getting lost in the noise.

That's why Winding Oaks exists. As a local consulting agency we bring insider knowledge of these dynamics—not just theory, but real-world insight into what works here. Whether you're navigating rapid expansion, outpacing competitors, or simply seeking clearer financial and operational systems, we are your partner in turning Hill Country opportunities into sustainable success.