Structuring the sale of your business to preserve your assets and legacy.
Many entrepreneurs looking to sell their business are unaware of how many options they have in structuring that sale and the profound differences those different paths can make. A well-planned sale can save thousands—or even millions—of dollars in taxes and lay the foundation for lifelong security, comfort, and opportunity for yourself and your family. “Making the wrong choice could be one of the biggest regrets of your life,” says Andrew Ryan Hall, Vice President and Fiduciary Advisorwith Whittier Trust Company of Nevada. “But with some foresight and planning, it’s possible to set a course for the best outcome.”
As part of the Reno office of the oldest multi-family office headquartered on the West Coast, Whittier Trust, Hall gives clients the advantage of working within Nevada tax and trust laws while having access to a multi-state fiduciary team and network of attorneys, tax experts, and other advisors. He offers three pieces of advice for West Coast business owners who are anticipating a major liquidity event.
Start Planning as Soon as Possible
If you are like many first-time sellers, a majority of your net worth may still be tied up in the business itself. You may not yet have a full team of advisors—tax experts, estate planners, and fiduciary partners—because your focus has rightly been on building and positioning the company for a successful sale. But in truth, the earlier you begin thinking about life after liquidity, the better equipped you will be to make decisions that minimize tax exposure and align your wealth with your long-term goals.
“It's a chicken-and-egg question,” Hall says. “How do you surround yourself with the right people and resources before the ‘egg’ is in the picture? The answer is to begin educating yourself as early as possible so you have time to get referrals, do research, and have honest conversations with people you can trust to help guide your success. Failing to employ the best professionals ahead of time can be a costly mistake. There’s no undo button on certain decisions.”
Ideally, you’ll be able to plan as much as five years ahead of time, which would allow you to consider and compare solutions such as a C-Corp structure along with a qualified small business stock (QSBS) solution. But even if your timeline is more constricted, there are alternate solutions that can work to minimize your tax burden and optimize your net payout.
Consider All Options to Minimize the Tax Hit
Once you've sold your business, you could be paying a shockingly large tax bill depending on how you’ve structured the company and the sale. “If you're in a state like California that has a higher capital gains tax, you could be paying up to a 13.3% premium on top of federal taxes,” Hall explains. “But there are solutions that give you a lot more bang for the buck, while allowing you to support your lifestyle and create a legacy for your family and maybe the broader community.”
A charitable remainder trust gives you a steady cash flow while deferring the capital gains that would have been realized, allowing assets to grow and providing an opportunity to implement your charitable goals.
A non-grantor trust has the benefit of mitigating state long-term capital gains taxes while taking care of designated family members or other beneficiaries.
A family limited partnership can facilitate the transfer of assets and wealth between generations, potentially reducing gift and estate taxes, provided you have time to plan in advance.
Setting up an irrevocable trust in Nevada could effectively avoid state capital gains tax on your sale because Nevada has no state or corporate income tax. We can coordinate with your attorney on implementing these types of estate strategies.
Define Your Personal Goals
We know that planning for a sale can be all-consuming. Even if you have a number of experts advising you, sometimes that advice results in an overwhelming confluence, or even conflict, of guidance. At Whittier Trust, we take a holistic approach, listen to your concerns and expectations, and help you take a step back to make sure you can confidently achieve your goals by crafting solutions that last generations.
“Taxes are only one slice of the pie,” says Hall. “We also want to know how you hope to use your assets and what impact you hope this sale will have on your legacy. We see the whole map and make sure that you’re getting to the right destination by coordinating proactively with all the different professionals needed. Together, we help create the best map for you, then keep you on track to accomplish that goal, using best practices to get the optimal outcome.”
If you’re ready to explore Whittier Trust’s family office services, start a conversation with a Whittier Trust advisor today by visiting our contact page.
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Whit Batchelor sat down with the San Diego Business Journal to discuss Whittier Trust's newest office.
Whittier Trust, a Pasadena-based wealth management company that serves "ultra-wealthy" clients, is opening a San Diego County office in Carmel Valley.
Founded in 1989 by the Whittier Family, which includes Helen Woodward of the animal shelter fame and philanthropist Paul Whittier, the firm has signed a three-year sublease for about 7,000 square feet of space on the second floor of an office building at One Paseo. "It will be our first brick-and-mortar office in San Diego (county)," said Whit Batchelor, the Whittier Executive Vice President who heads the San Diego County office.
"We're super excited about having a more visible local presence," Batchelor said.
Managing $25 billion in assets, Whittier Trust serves more than 600 families in 48 states, according to Batchelor, with about a dozen clients in San Diego County.
"They're all some of the most affluent families in San Diego," Batchelor said.
Whittier chose One Paseo for its San Diego County office because its local clients are concentrated in North County, primarily Rancho Santa Fe, Del Mar, La Jolla and Solana Beach, Batchelor said.
The firm is spending $400,000 to $500,000 on tenant improvements, most of which Batchelor said will be for redoing the lobby.
He said his goal is to add two to three new San Diego clients annually and gradually expand the San Diego office from its initial staff of six to seven professionals to about 30 over the next 10 years.
"We want to grow and partner with the right families in San Diego," Batchelor said. "One thing our clients all have in common is that they have big balance sheets."
Whittier Family History of Giving Back
To become a Whittier client, someone must have liquid assets of at least $15 million and pay annual dues of $150,000, Batchelor said.
"We think that San Diego is a fantastic market for our services," Batchelor said, adding that they include everything from real estate investments to managing stock portfolios and charitable donations.
"For us, being part of the community means giving back to the community. A big part of what we do is facilitate our clients' philanthropy," said Batchelor, who lives in Point Loma.
Paul Whittier, who died in 1991, focused much of his philanthropy on such San Diego institutions as Scripps Memorial Hospitals, the San Diego Maritime Museum, the Zoological Society of San Diego, and the Aerospace Museum.
Whittier Trust traces its history back to the early 1900s when Max Whittier, a former Maine potato farmer, moved west and made his fortune in real estate and petroleum.
His company, Belridge Oil Company, was sold to Shell Oil in 1979 for $3.65 billion, which was a record at the time, according to the Whittier Trust website.
Featured in San Diego Business Journal. Author Ray Huard interviews Whit Batchelor, Executive Vice President, Client Advisor, San Diego Regional Manager.
For more information on the new office or to start a conversation with a Whittier Trust advisor today, visit our contact page.
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Whittier Trust further strengthens its rapidly growing San Diego team with veteran trust and estates advisor, Kiley Barnhorst MacDonald.
Whittier Trust is pleased to welcome Kiley Barnhorst MacDonald as Senior Vice President and Client Advisor, based in the firm’s new San Diego office. With more than 30 years of experience at the intersection of the legal, corporate, and nonprofit sectors, Kiley is a trusted advisor to ultra-high-net-worth individuals and families. She is widely respected for her ability to navigate complex family dynamics and multigenerational planning with a steady hand and thoughtful, practical insight.
A San Diego native and fifth-generation Southern Californian, Kiley brings a coveted combination of legal acumen, strategic planning, and financial analysis to her work, tailoring each relationship to reflect the specific values and goals of the individuals and families she serves. Her multidisciplinary background allows her to approach wealth management with both technical depth and a personal touch.
“Kiley brings the kind of deep expertise and authentic connection that makes a lasting impact,” said Whit Batchelor, Executive Vice President, Client Advisor, and San Diego Regional Manager at Whittier Trust. “She’s already a trusted voice in our community, and her arrival is a meaningful step forward in building our San Diego presence with intention and care.”
Before joining Whittier Trust, Kiley served as Senior Vice President, Senior Trust Advisor at Northern Trust Wealth Management. She also practiced in La Jolla at Albence & Associates and the Law Offices of W. Neal Schram. Kiley holds a JD from UCLA School of Law and a BA in Economics from Dartmouth College. She is a California State Bar Certified Specialist in Estate Planning, Trust, and Probate Law.
Beyond her professional accomplishments, Kiley is a dedicated community leader who has served on the boards of several nonprofit and educational organizations. She has been recognized by the Legal Aid Society for her pro bono efforts supporting families in probate court.
Whittier Trust opened its San Diego office earlier this year to meet the needs of a growing client base in the region. With Kiley now on board, the firm continues to build a team of top-tier professionals who combine technical excellence with an unwavering commitment to client service.
For more information about Whittier Trust, start a conversation with an advisor today by visiting ourcontact page.
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Anna Peterson’s addition to the San Diego office reflects continued growth and demand for personalized wealth services in the region.
Whittier Trust is pleased to announce the hiring of Anna Peterson as an Assistant Vice President, Client Advisor in the firm’s expanding San Diego office. Anna brings a depth of experience in estate planning and family office advisory that aligns with Whittier’s commitment to thoughtful, high-touch client service.
In this role, Anna serves as a strategic advisor to high-net-worth individuals and families, delivering bespoke family office services that integrate generational wealth transfer and tax-optimized strategies. Her collaborative approach and ability to navigate complex wealth structures make her a valuable addition to Whittier Trust’s advisory team.
“Anna’s background working with ultra-high-net-worth families and her expertise in multifaceted estate planning make her a natural fit for Whittier Trust,” said Whit Batchelor, Executive Vice President, Client Advisor, and San Diego Regional Manager at Whittier Trust. “As we continue to grow our presence in San Diego, Anna strengthens our ability to deliver tailored advice that reflects both the complexity and individuality of our clients’ financial lives.”
Prior to joining Whittier, Anna was a key member of the Family Office team at ICONIQ in San Francisco, where she advised families with assets ranging from $100 million to over $1 billion. She holds both the Certified Financial Planner™ (CFP®) and Certified Trust and Fiduciary Advisor (CTFA) designations and earned her Bachelor of Arts & Sciences from Boston College.
Whittier Trust’s San Diego office has seen steady momentum, reflecting the broader demand for integrated, relationship-driven wealth management in Southern California. Anna’s arrival further bolsters the firm’s ability to meet that demand with sophisticated, multi-generational planning and advisory capabilities.
For more information about Whittier Trust, start a conversation with an advisor today by visiting ourcontact page.
From Investments to Family Office to Trustee Services and more, we are your single-source solution.
Whittier Trust Grows San Diego Team and Fortifies Its Commitment to the Entrepreneurial Spirit with the Addition of Ted Fogliani.
Whittier Trust is pleased to announce the addition of Ted Fogliani as Vice President of Business Development in the firm’s San Diego office. A veteran entrepreneur and former CEO with over 25 years of experience building successful companies in eCommerce, SaaS, manufacturing, and logistics, Ted brings a dynamic mix of strategic vision, operational leadership, and a deep-rooted commitment to client service.
Ted joins Whittier Trust after serving as Founder and CEO of ShipCalm, a tech-enabled logistics company supporting eCommerce brands. There, he played a critical role in shaping the company’s growth strategy, culture, and customer-centric approach to supply chain management. Prior to ShipCalm, Ted spent two decades as Founder and CEO of a leading electronics manufacturing company, overseeing the production of medical devices, consumer electronics, and critical national defense systems.
“Ted’s background as a founder and operator gives him a unique lens into the needs, concerns, and aspirations of the entrepreneurs and business owners we serve,” said Whit Batchelor, Executive Vice President, Client Advisor, and San Diego Regional Manager at Whittier Trust. “He’s walked in their shoes. That perspective, combined with his strategic acumen and leadership experience, makes him a powerful advocate for our clients and a natural fit for our team.”
Throughout his career, Ted has championed the idea that long-term value is built by hiring great people and rallying them behind a clear vision. At Whittier Trust, he’ll focus on fostering meaningful relationships with families and founders across Southern California, helping them navigate the complex intersection of personal wealth and business leadership.
A lifelong Californian and long-time resident of the San Diego area, Ted and his wife Monica have raised their four children in Carmel Valley and Del Mar. They remain active in the community and are passionate supporters of organizations such as the San Diego Police Foundation and Boys to Men Mentoring.
For more information about Whittier Trust, start a conversation with an advisor today by visiting ourcontact page.
From Investments to Family Office to Trustee Services and more, we are your single-source solution.
Celebrating its 25th anniversary in 2025, the Whittier Trust Seattle Office continues to grow and strengthen its family office services with experienced CPA, Philip Cook.
Whittier Trust is proud to welcome Philip Cook as Vice President and Client Advisor in the firm’s Seattle office. A seasoned advisor with more than 18 years of experience in tax, estate planning, trust administration, and family governance in both California and Washington State, Philip joins the Pacific Northwest team of The Whittier Trust Company of Nevada, where he will serve ultra-high-net-worth families in both Seattle and Portland.
Philip brings to Whittier Trust a distinctive blend of technical expertise and personal insight, shaped by 12 years in public accounting with time at Deloitte and Andersen Tax, followed by six years as Director and Senior Director at Pacific Trust Company. There, he led the firm’s consulting practice, guiding families through the most complex aspects of estate structures, fiduciary oversight, and multi-generational planning.
“Philip's background as a CPA, combined with his leadership in trust and estate advisory work, aligns perfectly with Whittier Trust’s integrated and personalized approach,” said Nick Momyer, Northwest Regional Manager, Senior Vice President, and Senior Portfolio Manager at Whittier Trust. “He has a great ability to balance analytical rigor with a deep understanding of family dynamics, qualities that are central to the work we do.”
As Whittier Trust celebrates 25 years of service in Seattle and 60 years of dedication to the Pacific Northwest in 2025, Philip's arrival underscores the firm’s continued investment in its Seattle office and long-standing commitment to delivering comprehensive family office solutions across the region.
Philip holds a Bachelor of Arts in Economics from the University of California, Santa Barbara, and a Master of Accountancy from California State University, Fullerton. He is a licensed Certified Public Accountant (CPA) in Washington State. Originally from Southern California, Philip has called Seattle home since 2014, though he continues to spend time in Southern California working with clients and visiting family.
For more information about Whittier Trust, start a conversation with an advisor today by visiting ourcontact page.
From Investments to Family Office to Trustee Services and more, we are your single-source solution.
JoshElcik’s appointment reflects continued growth and a firm-wide commitment to a secure and seamless digital experience for Whittier Trust clients.
Whittier Trust is pleased to announce the addition of Josh Elcik as Senior Vice President and Director of Information Technology. A seasoned technology executive with more than two decades of experience leading at the intersection of innovation and operational strategy, Josh brings a depth of expertise in designing and implementing enterprise technology systems. He will be based in the firm’s Pasadena office.
Josh’s appointment comes at a time of meaningful expansion for Whittier Trust. As the firm continues to grow, so too does the demand for technology that is not only secure and scalable but also intuitive and responsive to the evolving needs of clients and their advisors.
“Josh joins Whittier Trust with a mandate to further modernize and fortify the systems that underpin our business,” said Thomas J. Frank Jr., Whittier Trust Executive Vice President and Northern California Regional Manager. “His leadership will help ensure we continue delivering the high-touch service our clients expect, supported by the kind of thoughtful, future-ready infrastructure that quietly powers it all.”
Over the course of his career, Josh has led large-scale digital initiatives across diverse industries, including financial services, energy, and media, each with a focus on long-term efficiency and enterprise agility. He is known for building high-performing global teams, championing cross-functional collaboration, and architecting integrated platforms that elevate both performance and compliance.
“I’m drawn to Whittier Trust’s legacy of excellence and its culture of precision and care,” said Josh Elcik. “Technology is most effective when it disappears into the background, empowering people to do their best work, and enabling clients to experience a seamless, secure relationship with their advisors. That’s the standard, and that is what we’re always building toward.”
Josh earned his degree in Management Information Systems from Texas Tech University. He maintains a deep interest in emerging technologies, data governance, cybersecurity, and adaptive organizational strategy.
Josh’s appointment reflects Whittier Trust’s ongoing investment in people, systems, and strategies that sustain exceptional client service in a complex and fast-moving world.
For more information about Whittier Trust, start a conversation with an advisor today by visiting ourcontact page.
From Investments to Family Office to Trustee Services and more, we are your single-source solution.
In a recent roundtable discussion hosted by the San Diego Business Journal, Whit Batchelor, Executive Vice President and San Diego Regional Manager at Whittier Trust, joined fellow Southern California wealth management professionals to address the most pressing questions facing clients today.
How do I strategically incorporate philanthropic vehicles like a donor-advised fund or family foundation into my comprehensive wealth management plan and overall asset allocation?
Integrating philanthropy into your wealth management strategy requires thoughtful coordination between your giving goals and tax planning. Private foundations and donor-advised funds offer powerful legacy-building opportunities, but with important distinctions in tax treatment and governance that must inform your selection.
Strategic asset selection can significantly enhance tax efficiency. Non-income producing assets like car collections, vacation properties, or significant artwork often represent ideal philanthropic contributions–potentially providing substantial deductions while converting non-cash-flowing assets into charitable impact. We approach this holistically, viewing your wealth across three dimensions: assets inside your estate, outside your estate, and within philanthropic entities.
This integrated perspective allows us to optimize your philanthropic impact while creating meaningful tax advantages and preserving family values across generations.
I’m considering splitting my time between California and other locations. What strategic tax planning approaches should I implement to legitimately minimize my California income tax exposure?
California residents approaching business transitions or retirement often have unique opportunities to optimize their tax situation while fulfilling lifestyle goals. Strategic planning around residency can yield significant tax advantages–particularly when spending time in non-income tax states like Nevada, Washington, Texas, and Florida.
Proactively establishing non-California trusts or entities prior to significant liquidity events can dramatically reduce tax exposure when selling business interests. Similarly, establishing legitimate residency in no-income-tax states before drawing on retirement accounts can preserve substantial wealth.
We emphasize that “asset location” is as critical as asset allocation in comprehensive wealth planning. This includes thoughtful positioning of assets across various jurisdictions to leverage beneficial tax treatment both inside and outside high-tax states like California–creating long-term advantages while supporting your desired lifestyle.
I’ve built a substantial portfolio of investment real estate that has appreciated significantly, creating potential estate tax exposure. What sophisticated strategies would you recommend for transferring these properties to my children in a tax-efficient manner?
California’s remarkable real estate appreciation over recent decades has created both opportunity and challenge–with many families holding properties now exceeding lifetime estate tax exemptions. The goal becomes transferring these high-value assets to future generations while addressing several competing concerns.
Effective strategies must balance estate tax minimization with maintaining control and preserving cash flow during your lifetime, while also considering California’s property tax implications. Tools like Spousal Limited Access Trusts (SLATs), intentionally defective grantor trusts, and qualified personal residence trusts can be particularly effective.
Strategic discounting through family limited partnerships or LLCs can further enhance transfer efficiency. These sophisticated approaches allow significant real estate value to move outside your taxable estate while retaining income streams and influence–preserving both wealth and your desired lifestyle during retirement.
Our family’s wealth has grown substantially in both value and complexity. What solutions should we consider for streamlining this complexity and ensuring seamless continuity if either of us becomes incapacitated or passes away?
As family wealth grows in complexity, what was once intellectually stimulating can eventually become burdensome–especially as priorities shift toward lifestyle enjoyment rather than wealth management. This challenge becomes particularly acute when responsibility has primarily rested with one spouse, potentially creating significant stress for a surviving partner.
Multi-family offices provide an elegant solution by offering comprehensive services that address both investment management and administrative complexity. Services like bill payment, household accounting, bookkeeping, tax coordination, and compliance management create a seamless infrastructure that functions reliably regardless of family circumstances.
This integrated approach ensures continuity during difficult transitions and provides peace of mind that your affairs will be managed according to your wishes–protecting both your surviving spouse and future generations from administrative burdens that they may be unprepared or unwilling to shoulder.
Answers provided by Whit Batchelor, Executive Vice President and San Diego Regional Manager with Whittier Trust.
If you have more questions about philanthropic planning, real estate strategies, tax-efficient wealth transfers, or simplifying complex family finances, start a conversation with a Whittier Trust advisor today by visiting our contact page.
From Investments to Family Office to Trustee Services and more, we are your single-source solution.
What ultra-high-net-worth individuals need to consider when mulling an exit.
In my role at Whittier Trust, I've seen firsthand how critical it is for ultra-high-net-worth individuals (UHNWIs) to have a well-thought-out exit strategy for their family businesses. Despite the intensive planning that typically goes into wealth management, recent research from the Exit Planning Institute suggests that a staggering 80% of business owners lack solid exit strategies, leaving their wealth in limbo and risking economic continuity for future generations.
The planning process of an exit strategy can often be fraught with uncertainty and potential pitfalls, making it a critical issue for business owners nearing retirement or a transfer of ownership or leadership. Here are the five key questions UHNWIs should ask their advisors to ensure a smooth and successful transition.
1.How many different exit strategies are available to me?
Understanding the various ways you can exit is fundamental to choosing the right path for your business. Each exit strategy has unique implications and suitability depending on your business's circumstances and your personal objectives. Here's a breakdown:
Generational Family Transfer
When multiple generations of a family are actively involved in the business, an owner might prioritize business legacy and family engagement over the sale price. If the objective is to keep the business in the family, the exit plan might involve transferring company stock, often at a discount, to direct heirs over many years. While keeping a majority stake in the company and control over operations, the owner can transfer assets to the next generation while still mentoring and training the next leader.
A generational family transfer can play out in a variety of ways: the owner may ultimately sell stock in the company to family, retire holding minority ownership or gift all stock to heirs. A successful transfer will take at least three to five years to accomplish, position the business for success, meet the owner's liquidity and financial needs after the transfer and leave the new owner(s) financially stable after the transaction.
Management Buyout
An owner who wants to sell all or part of the company to existing management might favor a management buyout. This type of ownership transition involves structuring a deal in which management uses the assets of the business to finance a significant portion of the purchase price. This can work for an owner who believes in the management team and thinks it will be able to keep the business thriving when he/she exits. However, if the management team lacks adequate liquidity, the seller may have to accept a lower price or unattractive deal terms, including heavy seller financing.
Sell to Partners
When the owner has partners and a quality buy-sell agreement, a sale to partners may be the only selling option. A buy-sell agreement generally articulates a controlled process for transferring ownership. Since the buyers fully understand the business and it's a planned process, selling to partners generally isn't too expensive. Common challenges in selling a business to partners include a lower sale price, slow transfer of proceeds and potential disagreements among partners.
Sell to Employees (ESOP)
When an owner wants to sell the company to its employees, an employee stock ownership plan (ESOP) might be the answer. In this type of sale, the company uses borrowed funds to acquire shares from the owner and contributes the shares to a trust on behalf of the employees. ESOPs require a securities registration exemption and are classified as an employee benefit, so it's an involved process. An ESOP sale takes many years to complete and is generally more expensive and complicated than other options. However, it can be a way to reward valued employees with company ownership. The tax savings to the seller can be substantial as well.
Sell to a Third Party
When the business is healthy and the owner wants to cash out, selling to a third party could be a good option. Whether the interested party is a strategic buyer, a financial buyer or a private equity group, the owner should expect to pay some big up-front costs to engage experienced professionals to guide the owner and company through the selling process. Having the right partners attending to the owner's interests, negotiating with the buyer and structuring deal terms are crucial to achieving the best outcomes.
Although the payoff can be attractive, third-party sales are not for the faint of heart. The process takes at least nine to twelve months and can be intense and emotional for the seller. Often, the seller retains some obligation to the business beyond the sale but has to be ready to give up control entirely. A third-party sale is ideal for an owner who is open to having the buyer bring new energy, ideas and change to the business.
Recapitalization
An owner who is open to having outside investors fund the company's balance sheet might consider bringing in a lender or equity investor to act as a partner in the business. By selling a minority or majority position, the owner can partially exit, monetize a portion of the business and reduce ownership risk in the company. New growth capital can bring more earnings to the original owner. When ready to exit the company completely, the original owner might sell the remaining shares through further recapitalization or another exit option.
Selling any portion of the company to an outsider can precipitate a loss of control and a cultural shift within the company. An owner who is not ready to be accountable to partners should consider this before opting to recapitalize.
2. How long before retirement should I begin thinking about my exit?
Ideally, business owners should start thinking about their exit strategy at least five to ten years before their intended retirement. This period allows for comprehensive planning that can influence key outcomes of the eventual sale. Value-building initiatives need time to succeed and show results before they can impact sale proceeds (valuation optimization). Identifying and grooming a successor — whether a family member, a key employee or an external buyer — is generally most effective over an extended period (succession planning). Structuring the business and the sale to maximize tax efficiency and comply with legal requirements is an involved process (legal and tax planning). Finally, strengthening the business's operations and financial health can make it more attractive to potential buyers (operational improvements).
3. Whatsteps should I take to optimize valuation and transition?
Optimizing your business's valuation and ensuring a smooth transition involves several strategic steps. First, conduct regular financial audits to present clear and accurate financial statements; transparency is key to attracting serious buyers and securing a favorable sale price. Next, take a look at opportunities to enhance operational efficiency to demonstrate the business's profitability and growth potential. This might involve adopting new technologies, improving processes or cutting unnecessary costs. Another crucial step is to develop a strong management team that can operate independently, as a business that doesn't rely solely on the owner is more attractive to buyers. Solidifying relationships with key customers and suppliers is also important, since long-term contracts and stable relationships add value and stability to the business. Finally, ensure the business complies with all legal and regulatory requirements. Any outstanding legal issues can deter buyers or lower the sale price.
4. What if a big part of my exit is going to be a sale or a partial sale?
If you are leaning toward a sale, either partial or complete, several considerations come into play. Engaging professionals is one of the first and most crucial steps. Working with experienced legal, financial and business advisors helps owners navigate the complexities of the sale process. Those professionals can also help with due diligence. Buyers will conduct thorough examinations of every facet of your business, including financial records, legal documents and operational data. Being prepared with detailed and organized documentation can facilitate a smoother due diligence process and instill confidence in potential buyers. This preparation not only expedites the sale process but also helps in presenting your business as a well-managed and transparent entity, which can lead to a more favorable sale price.
Identifying potential buyers is also a strategic consideration that can greatly influence the sale’s success. Depending on your business's nature and industry, potential buyers could be competitors, private equity firms or even international investors. Identifying and approaching the right buyers ensures that you attract parties who see the most value in your business.
5. How should I structure sale deals?
Structuring a sale deal requires careful planning and negotiation to balance your needs with the buyer's. This involves key elements like payment terms, which can be a one-time lump sum or installments. You might even consider seller financing, which can make the deal more attractive but comes with the risk of the buyer defaulting. Another option is to structure earn-out payments tied to the business’s future performance, which can bridge valuation gaps but require clear metrics and timelines. Noncompete agreements are often requested by buyers to prevent owners from starting a competing business post-sale, so ensure the terms are reasonable and don’t unduly restrict future options.
The structure of the deal can also significantly impact your tax liabilities. Understanding the tax implications of different payment structures is crucial, as installment payments may help spread the tax liability over several years. Work with wealth management advisors to explore strategies that could mitigate your tax burden. Experienced legal counsel can help you draft and review all agreements, focusing on representations and warranties to minimize future liabilities and ensuring provisions for indemnification to protect against potential future claims or disputes.
You will also have to decide whether you'll stay involved in the business after the sale, in either a consulting capacity or a more formal role. This can ease the transition and provide additional income, but it might also limit your ability to fully step away. Don't forget to consider how the sale aligns with your personal and family goals. Reflect on how the sale proceeds will be integrated into your overall estate plan, ensuring the structure supports your legacy and philanthropic goals. Also assess how the sale structure impacts your lifestyle and plans, whether it involves retirement, new business ventures or other personal endeavors.
The transition of a family business is a complex process that requires careful planning and execution. By asking your advisors the right questions, you can ensure a smooth and successful exit that secures your legacy and financial future.
Written by Elizabeth Anderson, Vice President at Whittier Trust. Elizabeth is based out of the Pasadena office and focuses on family business transitions, succession planning and pre-liquidity personal planning.
For more information, start a conversation with a Whittier Trust advisor today by visiting our contact page.
From Investments to Family Office to Trustee Services and more, we are your single-source solution.
How smart entrepreneurs future-proof their legacy.
Most entrepreneurs who have built a corporation to a valuation in the hundreds of millions (or higher) will tell you about a beginning filled with hard work, sleepless nights and worry over whether or not their business would survive. We work with many family businesses that are now worth over a billion dollars, but they all started somewhere.
Those early days are the ideal time to strategize for future success by shielding yourself and your business from unnecessary tax burdens, maximizing the impact of your legacy and creating terms that fulfill your vision. However, many of those same entrepreneurs who are so good at building a business from the ground up fail to forecast 20 or 30 years into the future. They're too focused on the now. Unfortunately, by the time a business reaches the pinnacle of its success, it may be too late to fully take advantage of the opportunities that existed early on.
That's where an experienced multifamily office comes in: they are specialists in helping individuals, entrepreneurs and families think far ahead and lay the necessary groundwork for a best-case scenario. The goal is to maximize potential returns and help “future-proof” clients' legacies, allowing them to fully enjoy the fruits of their hard work.
Easing Tax Burdens
When a company isn't worth a fortune, it's easy to forget about what might happen when its value rises. One important step is to qualify for Qualified Small Business Stock (QSBS) when the business is worth less than $50 million. Setting up a business to qualify for the QSBS isn't overly challenging. The entity must be a domestic C Corp, at least 80% of the corporation's assets must be used to conduct one or more qualified trades and originally acquired stock must be held for a minimum of five years, among other requirements. However, this process must be diligently undertaken to ensure entrepreneurs can reap the benefits down the line.
With QSBS, 100% of the gain from a sale can be excluded from federal income tax (subject to certain limitations), which can amount to a fortune if a company is sold for a high value. A number of multifamily office — and, more specifically, those with robust trust services — can both serve in an advisory capacity and handle the execution of the necessary steps (such as engaging and managing the right tax and legal professionals), allowing the entrepreneur to focus on growing the business.
Location, Location, Location
If there's any flexibility regarding where a business is located, multifamily offices can help set owners up in the most tax-advantaged position. For example, businesses located in California are subject to one of the highest corporate tax rates in the nation at 8.84%. If the income is generated by California real estate or headquartered in California, there's no way to escape that rate.
However, if the business can be headquartered in a more tax-advantaged state such as Nevada, which does not levy a corporate income tax, it might be worth considering. To help smooth the generational transition, some families utilize a trust situs in Nevada to hold their shares of the business. Nevada situs can help avoid California income taxes and California capital gains taxes (which amount to 13.3%) upon the sale of the business.
Mitigating Future Estate Taxes
If businesses grow inside a taxable estate, the government takes 40% of the value upon the owner's passing. For entrepreneurs who are building a successful corporation, it can be beneficial to allocate some shares into a trust outside of the taxable estate, where they can grow in value without being subject to the estate tax. There are a variety of trusts that allow owners to reap the benefits of the assets during their lifetimes, while shielding the estate from an onerous tax burden.
Preserving Family Harmony
Finally, it may not be obvious, but it's important to coordinate the estate plans of all family members who are involved in the business to ensure that they are aligned with the overall succession plan. The goal is to put a master plan in place that balances financial, corporate and relational goals so that the business — and the family attached to it — will thrive in perpetuity.
Start Early for Maximum Benefits
If you're reading this and your business isn't (yet) close to the multimillion-dollar threshold, it's still important to take the time to be thoughtful about how you'll set it up for future success. You may be spending your days working on improving the current bottom line, managing staff and investing in refining your product and service offerings. Still, we've seen companies quickly catapult from a few million in assets to a much higher value, so it's important not to wait. Having a go-to team of advisors who can provide both strategy and execution to file necessary paperwork, think critically about the company's financial trajectory and maximize the benefits as it grows.
Written by Brian Bissell, Senior Vice President, Client Advisor in the Orange County office of Whittier Trust.
Featured in Family Business Magazine. To learn more about how Whittier Trust can support you, your family and your legacy through our family office services, start a conversation with a Whittier Trust advisor today by visiting our contact page.
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Many entrepreneurs looking to sell their business are unaware of how many options they have in structuring that sale and the profound differences those different paths can make. A well-planned sale can save thousands—or even millions—of dollars in taxes and lay the foundation for lifelong security, comfort, and opportunity for yourself and your family. “Making the wrong choice could be one of the biggest regrets of your life,” says Andrew Ryan Hall, Vice President and Fiduciary Advisor with Whittier Trust Company of Nevada. “But with some foresight and planning, it’s possible to set a course for the best outcome.”
If you are like many first-time sellers, a majority of your net worth may still be tied up in the business itself. You may not yet have a full team of advisors—tax experts, estate planners, and fiduciary partners—because your focus has rightly been on building and positioning the company for a successful sale. But in truth, the earlier you begin thinking about life after liquidity, the better equipped you will be to make decisions that minimize tax exposure and align your wealth with your long-term goals.
We know that planning for a sale can be all-consuming. Even if you have a number of experts advising you, sometimes that advice results in an overwhelming confluence, or even conflict, of guidance. At Whittier Trust, we take a holistic approach, listen to your concerns and expectations, and help you take a step back to make sure you can confidently achieve your goals by crafting solutions that last generations. 
