Play hard,
Plan smarter
Helping you
grow and succeed
Financial success requires a roadmap. Get clear, direct advice from people who understand the NIL landscape and the demands of an athlete's life. We help you define the purpose for your money, giving you the real-world experience you need to win financially.
Protection
Core Value 3:
Your NIL check is hard-earned. We help you protect it, keep more of it, and make every dollar work with intention.
Experience
Core Value 4:
Real guidance from people who understand the NIL world and athletes’ lives—no sales pitches, just advice built on what actually works.
Learn More About Skyward Financial
Hear more from Ross Stripling and Skyward Financial about our mission to serve you.
See Where Ross Has Been Featured
Solutions for
every need
Deal Structure & Advisory: Shaping Forward-Looking NIL Contracts
A big check today shouldn't limit your potential tomorrow. Our advisory services go beyond compliance, consulting with your legal team to structure NIL deals that are more financially forward-thinking. We help ensure compensation includes elements—like equity or future licensing rights—that drive investment and long-term growth.
Tax Planning: A Year-Round Strategy for Maximizing Earnings
Complex income requires sophisticated tax strategy. We provide expert, year-round tax planning for your entire financial picture—from NIL earnings and investments to future professional income. Our goal is to minimize your tax liability through strategic deductions, timely filing, and proactive planning, maximizing the money you retain and invest.
Long-Term Wealth and Financial Literacy: Converting Income into Independent Wealth
We don't just manage your money—we teach you how to command it. This pillar builds your core financial literacy and purpose. We create a hands-on roadmap for intelligent investing, establishing portfolios, and using the power of compounding interest to turn your temporary NIL earnings into lasting, independent wealth.
Risk & Asset Protection: Your Financial Defensive Line
An athlete’s financial stability is inherently exposed to career risks. We build your risk management foundation through comprehensive insurance and asset titling strategies. This ensures your hard-earned NIL capital, investments, and personal assets are protected from unexpected injuries, liabilities, and financial threats.
Built
Different
Financial planning that
keeps up with your game
Experienced in creating
lasting solutions for every need.
+500 (million)
Assets Managed
28
Average Years of Professional Advisory
94%
Annual Client Retention (%)
+532
Number of clients served
Turn Every Deal Into Leverage.
We don’t just review contracts — we sharpen them. From uncovering hidden upside to structuring smarter terms, we help you maximize earning power and keep more of every NIL dollar.
Stay Locked In. Build Real Wealth.
You handle the performance. We help you plan, invest, and grow your NIL earnings so today’s deals create momentum long after the season ends.
Advice You Can Trust.
Our guidance is transparent, objective, and aligned with your goals. No noise. No pressure. Just disciplined financial strategy designed to support smarter decisions at every stage.
Protected At Every Level.
NIL rules move fast. We move faster. Our expertise keeps your money clean, your eligibility intact, and your career built for longevity.
Stay focused
on your success
Get in touch with Ross Stripling himself
a high-profile athlete with high-level financial insight
who understands exactly where you’re coming from and where you want to go.
Your
financial playbook
Step 1: Analyze Your Situation
We analyze your contracts, tax profile, and goals to establish a clear baseline. This helps us identify potential financial risks and hidden opportunities.
Step 2: Develop Your Personalized Plan
A customized financial strategy is developed. This blueprint may include tax-efficient strategies and investment recommendations aligned with your objectives.
Step 3: Launch a Financial Plan
We coordinate the execution—assisting with account setup, aligning with your full support team, and activating your financial plan. You focus on performance.
Step 4: Ongoing Monitoring & Support
We continuously monitor your financial plan and review performance periodically, recommending proactive adjustments based on market shifts or rule changes.
We Get it
Less than 2% go pro.
Even fewer make the money last.
Financial literacy keeps you paid. Start here.
Hear more from Ross
Article: How an All-Star Dodgers pitcher went from baseball to business
Article: Toronto Blue Jays Arbitration Preview: How Much Will Teoscar Hernandez Cash In For?
Article: Baseball Is on Indefinite Hold. Pitchers Still Need to Keep Their Arms Ready.
Article: 26-year-old Dodgers rookie pitcher works as a stockbroker in the offseason
Article: LPL Nabs $700 Million Advisor Team From Wedbush Securities
Article: Jay trader: Toronto pitcher is a stocks whiz
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We should just talk
No pressure. Just a laid-back conversation about what’s next.