Looking Ahead — Learn to Make Better Financial Decisions

The Secret to Outpace the Competition? Your CFO | Ft. Peter Gregory | Looking Ahead EP 3

If you’ve ever wondered whether your business really needs a CFO—or what a fractional CFO can do that a full-time hire can’t—this episode is for you.Max Morgan sits down with fellow Lookahead Advisory partner Peter Gregory, Head of Strategy, to unpack how CFO-level strategy can transform a business’s trajectory. Drawing from decades of executive leadership, entrepreneurship, and advisory work, Peter shares why the CFO role often drives more strategic decision-making than the CEO, how to build financial models that actually guide growth, and the importance of cash flow planning that looks 12 months ahead—not just at last month’s numbers.From a barbershop turnaround story to navigating multimillion-dollar capital planning, Peter breaks down what it means to serve as the “CFO conscience” for business owners. You’ll learn how real-time financial strategy can help you grow faster, avoid costly mistakes, and create a clear path toward your long-term goals.Whether you’re a $1M business hitting your first major growth ceiling or running a $30M operation with no strategic finance lead, this conversation reveals why timing, clarity, and the right advisory partner matter more than ever.Chapters00:55 Meet Peter Gregory: Background and Experience02:59 The Role of a Fractional CFO03:44 Success Stories and Impact06:26 Strategy and Financial Planning11:20 Understanding Fractional vs. Full-Time CFO20:39 Onboarding and Client EngagementConnect With PeterWith over 30 years of experience as an executive, founder, investor, and CFO, Peter helps business owners align their strategy, financial operations, and personal goals. He specializes in building financial models that guide every major decision, ensuring clients have the clarity and confidence to grow sustainably. From early-stage companies to enterprises nearing $200M in revenue, Peter partners with leaders to make smarter moves, faster.Schedule a Call With Peter: https://calendly.com/peter-lookaheadConnect With MaxMax brings experience across startups and large asset management firms, helping executives and business owners plan, operate, and scale with clarity. His work spans retirement, education, and generational wealth planning, with a focus on building clear, actionable financial roadmaps that support every stage of growth.Schedule a Call With Max: https://calendly.com/maxmorg About Lookahead AdvisoryLookahead Advisory helps individuals, families, and business owners navigate long-term financial decisions with clarity, transparency, and a clear head. Our services include:- Financial planning- Wealth management- Tax strategy- Business planning- Fractional CFO supportWe don’t sell products—we offer perspective. Whether you’re building wealth, preparing for retirement, or scaling your business, we’re here to help you make smarter, calmer financial decisions.Schedule a check-in with our team: https://lookaheadadvisory.com/contact/

How Real Tax Strategy Saves You Thousands (and Your Sanity) | Ft. Lorilyn Wilson | Looking Ahead EP 2

If your CPA only shows up at tax time, you're leaving money on the table. In this episode, Max Morgan sits down with fellow Lookahead Advisory partner and Head of Tax & Accounting, Lorilyn Wilson, CPA, to unpack what real, year-round financial strategy looks like—and why aligning your tax planning with your wealth goals is the smartest move you can make. They dig into Lorilyn’s path from college athlete to trusted advisor, the difference between tax prep and tax strategy, how to avoid common missteps as a business owner, and why Lookahead’s integrated model offers more than traditional advice ever could. Connect With Lorilyn For over a decade, I’ve guided hundreds of individuals and businesses through tax planning, compliance, and growth. She helps clients minimize liabilities, make sense of complex decisions, and build long-term strategies for wealth and success. Follow Lorilyn on Instagram & TikTok: @taxandwealth Twitter: @LorilynWilson Schedule a Call With Lorilyn: https://calendly.com/lorilynwilsoncpa/15-minute-consulting-call [https://calendly.com/lorilynwilsoncpa/15-minute-consulting-call]  Connect With Max Max brings experience across startups and large asset management firms, helping executives and business owners plan, operate, and scale with clarity. His work spans retirement, education, and generational wealth planning, with a focus on building clear, actionable financial roadmaps that support every stage of growth. Schedule a Call With Max: https://calendly.com/maxmorg [https://calendly.com/maxmorg]  About Lookahead Advisory Whether you’re building a business, balancing multiple income streams, or just want to stop scrambling every April, this conversation is packed with actionable takeaways. Lookahead Advisory helps individuals, families, and business owners navigate long-term financial decisions with clarity, transparency, and a clear head. Our services include: * Financial planning * Tax strategy * Wealth management * Business planning * Fractional CFO support We don’t sell products—we offer perspective. Whether you’re building wealth, preparing for retirement, or scaling your business, we’re here to help you make smarter, calmer financial decisions. Schedule a check-in with our team:https://lookaheadadvisory.com/contact/ [https://lookaheadadvisory.com/contact/]

How to See the Financial Future of Your Business | Ft. Kathy Gregory

If you’ve ever confused profitability with cash flow—or wondered why your bookkeeping doesn’t help you make smarter business decisions—this episode is for you. In this conversation, Max Morgan sits down with fellow Lookahead Advisory partner Kathy Gregory, Head of Business Forecasting, to unpack what real financial planning looks like for business owners. Kathy shares how she helps entrepreneurs go beyond compliance and accounting, using financial modeling to clarify performance, guide smarter spending, and support long-term growth. By the end of the conversation, you’ll learn how business owners can stop guessing, start planning, and finally feel confident about the road ahead. Whether you’re running a $500K company or managing multimillion-dollar growth, Kathy breaks down what makes the biggest difference in business forecasting and why every founder needs a financial model they can actually use. About Lookahead Advisory Lookahead Advisory helps individuals, families, and business owners navigate long-term financial decisions with clarity, transparency, and a clear head. Our services include: * Financial planning * Tax strategy * Wealth management * Business planning * Fractional CFO support We don’t sell products—we offer perspective. Whether you’re building wealth, preparing for retirement, or scaling your business, we’re here to help you make smarter, calmer financial decisions. Schedule a check-in with our team: https://lookaheadadvisory.com/contact/ [https://lookaheadadvisory.com/contact/] Additional Resources * Guide: Benefits of a Financial Forecast for Your Business [https://lookaheadadvisory.com/the-benefits-of-a-financial-forecast-to-your-small-business/] * Guide: Why Growing Businesses Need a Better Budget [https://lookaheadadvisory.com/your-growing-business-needs-a-better-budget/] * Guide: How to Make Your First Financial Forecast [https://lookaheadadvisory.com/want-to-make-your-first-financial-forecast-heres-a-4-step-playbook/]