
Insights
Clarity for the Road Ahead
Every founder eventually faces the same question: what comes next? Whether you’re preparing to sell, raise capital, or hand the business to the next generation, the decisions aren’t easy, and the advice shouldn’t be generic.
At Peninsula Road, we work with owners every day, navigating these decisions. This collection reflects what we’ve learned, and what we think is worth sharing.
Selling Your Business
Selling a business isn’t just a financial decision; it’s a personal one. You’ve built something valuable, and now you’re thinking about what comes next. This collection is built to help you explore that choice, with insights on M&A mechanics, working with an advisor, maximizing value, and navigating diligence without losing momentum.
Most business owners believe normalized EBITDA is essentially "here's why I'm worth more than I show the tax man." But buyers are rebuilding your org chart with market-rate compensation, and frequently, those adjustments erase more value than your add-backs create. Here's how to see what they see, before it's too late.
Not every owner dreams of selling. But most eventually wonder. This article explores why the idea starts to surface and why acting from strength can lead to the best outcome.
Buyers only see the polished pitch and the final offer, but what drives real outcomes is the strategy, prep, and process that happens behind the scenes. This article unpacks why the best deals don’t happen by accident, and what work fees are really paying for.
Buyers are hesitant. Deals are taking longer. But for owners without a clear transition plan, this might be the right moment to prepare before the market shifts again.
The structure of your deal, not just the price, determines how much you really walk away with. This guide explains key components like earnouts, seller notes, and working capital, helping business owners plan for real outcomes, not just headline numbers.
What’s your business worth? More importantly, what can you do to make it worth more? This article breaks down five key drivers that influence how buyers view (and value) your company.
When business owners think about selling, one of the first questions they ask is: “What will this cost me?” This article breaks down how M&A advisor fees actually work and what you’re really paying for when you hire the right partner.
Valuation isn’t just about earnings, it’s about how a buyer sees the next five years. In this article, we break down what actually drives value and why comparing your business to someone else’s “multiple” can lead you astray.
When we asked business owners about their biggest challenge in selling, 60% said it’s the emotional hurdle of letting go. In this article, we explore why it’s so difficult to step away — and how to prepare yourself for this inevitable part of the journey
Preparing your business for sale isn’t just about finding a buyer—it’s about setting the stage for a successful transaction. From financial cleanup to operational improvements and legal readiness, these steps will help you maximize value and ensure a smooth sale.
This practical guide breaks down the M&A process into six clear steps, from planning and valuation to negotiation and closing. Designed for business owners preparing for a sale, it outlines what to expect at each stage and how the right advisors can help ensure a successful outcome.
Overreliance on the owner, especially for revenue, is one of the most common reasons businesses are undervalued or deals fall apart. Learn how to reduce key person risk and increase buyer confidence.
Are you considering selling your family business? Discover the essential guide to navigating this significant decision. From preserving your legacy to planning for the future, unlock the insights and strategies you need for a successful transition.
Many owners prepare their business for sale, but not themselves. This article explores the emotional transition that follows an exit and why finding clarity about what comes next takes time.
An unexpected offer to buy your business can be flattering or overwhelming. In this article, we break down what unsolicited offers really mean, how to respond strategically, and when to bring in outside guidance.
Hiring an M&A-specific advisor can provide numerous benefits, including expertise, experience, and an extensive, specialized network. At Peninsula Road, we understand the importance of an operator-friendly approach to divestitures, leveraging our experience to provide practical and tailored guidance to meet your needs.
Selling a business can be a tough decision to make. It involves several considerations, including financial and legacy concerns. Here are the top three things to consider before selling your business.
Succession Planning
Keeping the business in the family is about more than legacy; it’s about clarity, timing, and trust. Whether you’re planning for retirement or watching your children step into new roles, these articles offer honest insight into what it takes to navigate a family transition well.
Passing the business on to your children might feel like a natural next step, but it’s still a decision, not a default. This article explores how to structure a family transition, prepare your successor, and protect relationships along the way.
You’re in the seat. Now what? This is for next-gen leaders navigating self-doubt, earned responsibility, and the reality that nobody ever truly feels “ready.”
You’re not just doing a job; you’re stepping into a succession plan that no one has named yet. If you’ve joined the family business but aren’t in charge (and aren’t just staff either), this guide is for you. Learn how to lead from the second row, build trust without a title, and navigate the in-between with clarity and patience.
In many family businesses, the founder stays at the helm far longer than planned. It often comes from love or fear, not ego, but the cost is real: stalled leadership, rising resentment, and lost value. This article examines why it occurs and how both generations can move forward with greater clarity.
Every transition starts long before a formal plan. This guide helps founders open the door to honest, early conversations with their kids about the business and the future
If you want the business to stay in the family, it needs more than hope. This guide walks through how to talk, plan, and build toward a thoughtful transition.
Governance can play a crucial role in the success and continuity of family businesses. It provides a framework for preserving the family legacy, introducing professionalism, resolving conflicts, managing talent, ensuring financial transparency, and fostering long-term sustainability.
Raising Capital
Whether you’re exploring private equity, venture funding, or bank debt, raising outside capital changes the shape of your business and your role in it, these articles explore when capital makes sense, what it really costs, and how to align structure with strategy.
Raising capital can be a smart strategic move or a fast track to complexity. Before you bring someone new to the table, make sure it gets you closer to the future you actually want.
Navigating the complex startup landscape requires guidance from seasoned advisors. Explore the key qualities to seek, compensation strategies, alignment, and the importance of diverse opinions.
In this article, we'll delve into the economic model of venture capital funds, explore the compensation structure for general partners, and shed light on the expected returns.
Beyond the Sale
Legacy isn’t just what you leave behind; it’s how you prepare the people you care about to carry it forward. Whether you’ve already sold, are building toward a transition, or want your wealth to serve a purpose, these articles explore what it means to steward a legacy with intention.
Every business reaches a fork in the road. Whether it’s growth, succession, or personal priorities driving the shift, what comes next deserves careful thought. This is where clarity starts.
Selling your business is a milestone, but leaving it can feel like losing a part of yourself. In this reflection, I share what surprised me most after our sale, what I wish I’d done differently, and why preparing for life after the deal is just as important as the deal itself.
Legacy doesn’t happen by accident. In Part 5, we make the case for stewardship as a choice and offer a roadmap for preparing your family with intention.
Timing matters more than amount. This article explores setting expectations early, managing complexity, and deploying wealth with purpose, not hesitation.
You don’t have to give up control to start preparing your children for wealth. Part 3 shares five simple, proven ways to build financial readiness today.
Sudden wealth without context creates risk. Part 2 explains why heirs struggle and how to build financial “muscle memory” before the money arrives.
Most business owners worry about creating entitled heirs. But avoidance causes more harm than access. Part 1 explores why preparation protects legacy.
A deeply practical guide for business owners and family leaders navigating wealth transitions. Learn how to prepare your children, set expectations, and protect your legacy.
Selling a family business brings new opportunities and new responsibilities. This article outlines how to manage post-sale liquidity with the same discipline used to build the business, ensuring the long-term preservation of wealth, values, and family alignment.
In this article, we'll explore the unique characteristics of family offices, their investment strategies, and the diverse range of investment options they pursue. If you’re pursuing an investment and think a family office might be the right partner for you, hopefully this article will shed some light on who they are and how they operate.