1장
The Entrepreneur's Playbook: Building a Business from Scratch to Success
What separates successful entrepreneurs from those who struggle? Is it innate talent, luck, or something more fundamental? In "Self-Made Boss," Jackie Reses and Lauren Weinberg distill wisdom from their extensive work with small businesses at Square, offering a comprehensive roadmap for entrepreneurial success. The book draws from Reses' experience leading Square's lending division and her childhood growing up in her parents' pharmacy, combined with Weinberg's insights from working with resilient business owners during the COVID-19 pandemic. Praised by Mark Cuban as "the ultimate guide for entrepreneurs," this book has become required reading in business schools nationwide. Whether you're considering your first venture or looking to scale an existing business, the authors' practical, battle-tested advice cuts through the noise with actionable strategies that real entrepreneurs have used to build thriving enterprises.
2장
Finding Your Entrepreneurial Why
Every successful business begins with a compelling reason to start. Bobby Crocker, a former professional baseball player, launched his personal training business after a career-ending injury, motivated by his desire for independence-a value instilled by watching his father run a construction company. For Aylon Pesso, joining his father's ice cream shop in Queens meant carrying on a family legacy while bringing fresh ideas to their operation. Peter Stein transformed his lifelong passion for oysters into Peeko Oysters after being laid off, drawing on childhood memories of fishing with his father on Long Island.
Life transitions often spark entrepreneurial journeys. When Jen Pratt's employer Coldwater Creek closed in 2014, she leveraged skills learned from her florist mother to launch Fresh Sunshine Flowers-not as a traditional shop with high overhead, but from a customized box truck she had operational within just two months. Some entrepreneurs are driven by community needs, like Erin Caudell and Franklin Pleasant who founded The Local Grocer in Flint, Michigan to provide access to safe, nutritious food after the city's water crisis.
Others build businesses to fill gaps they personally experience. Photographer Lucia Rollow created Bushwick Community Darkroom after finding herself unable to afford darkroom access post-graduation. Starting with a $75 monthly storage space in her building's basement, she discovered many others shared her need. The business quickly grew into a full facility serving about 500 photographers monthly.
Despite their diverse origins, all small business owners face similar fundamental challenges: setting up finances, legal incorporation, hiring help, running operations, building brands, planning growth, and overcoming obstacles. What's remarkable is how these universal challenges manifest across wildly different industries-whether you're selling ice cream like Aylon or oysters like Peter.
Fortunately, entrepreneurs don't have to figure everything out alone. The Small Business Administration (SBA) offers invaluable free resources at every stage. As Bill Briggs, former SBA administrator notes, "The SBA is the best-kept secret in the federal government." Beyond federal resources, local chambers of commerce and specialized demographic-focused organizations provide targeted support. Most cities offer free public resources accessible through municipal websites or simple online searches.
Before taking the entrepreneurial leap, ask yourself: Will you thrive as your own boss? What passions might become careers? What businesses do you wish existed that you could create? Do you have adequate support networks? Can you handle the uncertainty of entrepreneurship? Your answers will reveal whether you're ready for the challenging but potentially rewarding journey ahead.
3장
Creating Your Business Blueprint
Michael Lassner learned the hard way that running a business without a plan leads to misalignment and conflict. After starting Allied Steel Buildings with a partner whose vision differed from his own, Michael eventually bought out his partner and implemented comprehensive planning processes. Today, he maintains "plans within plans" that guide his company's strategic direction and tactical execution.
With only half of small businesses surviving their first five years, a solid business plan dramatically improves your chances of success. Even if you're not seeking external funding, the research and thinking required to create a plan is invaluable. A business plan forces you to systematically think through your venture's viability before committing resources.
Start with a compelling executive summary that concisely captures why your business will succeed, highlighting the problem, solution, and target audience. Though brief, it's perhaps the most critical section, serving as a "greatest hits" introduction to your plan. Write it last to ensure it effectively distills the document's key points.
Before committing to a solution, thoroughly research and understand the problem you're solving. As Yvonne Cariveau advises, "Define your problem very, very specifically. Observe. Ask open-ended questions." Many entrepreneurs "fall in love with their solutions before they really understand the problem." Verify that your problem is worth solving, that customers will pay for your solution, and that your approach improves upon competitors'.
Detail how you'll actually produce your product or deliver your service, including materials, manufacturing methods, facilities, equipment, staffing, and location plans. Zellee, a Hawaii-based plant-based fruit snack company, experienced significant operational challenges, cycling through multiple manufacturers before finding the right partner. Your business plan should include contingency plans for production and sourcing-Lisa O'Kelly of Zellee recommends finding multiple suppliers and consulting with other businesses in your space about manufacturing options.
You must understand your exact production costs to determine viable pricing. Without knowing unit costs, you can't set profitable prices-as Yvonne Cariveau notes, "If you have a business where it costs you $100 to make an item and you can only sell it for $90, then you might as well just create an organization that gives $10 to every person you meet." Use benchmarking data from competitors to establish realistic pricing, then calculate potential sales by estimating market size, conversion rates, and customer acquisition.
Beyond simple flyer distribution, effective marketing requires tapping into networks, building online presence and social media, forming partnerships with other small businesses, and exploring advertising opportunities. Marketing strategy should prioritize products with the highest profit margins first, and consider both customer acquisition and retention strategies, as selling more to existing customers is easier than finding new ones.
Before fully committing, test your business concept in small settings like fairs or with potential clients. Pay attention not just to customer response but to your own enjoyment of the process-as Lisa advises, "Figure out if you even like to do this. Maybe you'll hate it!" Most businesses won't succeed if founders aren't passionate about the work.
You don't need expensive consultants to create a business plan. Free resources include the Small Business Administration and its small business development centers, local chambers of commerce, county and city government grants, retired industry professionals willing to coach, entrepreneur support groups, and your personal network. As Jen Pratt of Fresh Sunshine Flowers advises, "Think about your friend group. Who can help you? You don't have to do this on your own."
4장
Building Your Legal Foundation
Julie Newman of Jewel Branding in Atlanta brought on Ilana Wilensky as a partner after feeling like "a dairy farmer who needed to milk her cows every day." Though their partnership runs smoothly-with Ilana handling sales, marketing, and PR while Julie manages finance, operations, and processes-they still needed a formal written agreement when Ilana bought a third of the business with an option for another 15 percent.
Partnerships allow two or more people to own and operate a business together, sharing profits and losses. Partnership law expert Jeremy Weinberg recommends potential partners discuss key questions: What's your business vision? What will each partner contribute? How will you allocate income and losses? How much earnings will be reinvested versus distributed? What happens if a partner dies? How will the partnership eventually end?
A clear written agreement forces partners to address difficult questions upfront rather than postponing them until problems arise. Simple problems often sink partnerships, like Mike Yardley's experience where undefined earnings and rent payments destroyed both business and friendship. Others fail due to misaligned visions, as Michael Lassner discovered when he and his partner had opposing long-term goals.
One of your first legal decisions will be determining your company's corporate structure, which governs taxation, ownership division, and operational parameters. Each incorporation type offers different advantages and limitations.
The simplest business structure is a sole proprietorship, requiring minimal paperwork-just local licensing and possibly a DBA ("doing business as") document. As a pass-through entity, profits are taxed once on the owner's personal income tax return using Schedule C. The main drawbacks: you're personally liable for all business debts, and ownership is limited to one person.
Limited Liability Companies (LLCs) are slightly more complex than sole proprietorships but still manageable-cartographer Nat Case spent just two hours registering his LLC for under $150 total. LLCs offer significant benefits: multiple owners are allowed, profits are taxed just once as a pass-through entity, and most importantly, they protect owners' personal assets from business liabilities.
S corporations allow up to 100 shareholders (all must be US citizens or residents), separate business and personal liability, and single taxation of profits. They require more formalities than LLCs, including a board of directors, regular meetings, and record-keeping requirements. S corps offer advantages over LLCs: some investors prefer them, they're more familiar to advisors, and owners can receive both salary and dividends (potentially lowering overall tax burden compared to LLC owners' self-employment taxes).
C corporations are the ideal structure for businesses planning to sell shares publicly, allowing unlimited shareholders and multiple stock types. The major drawback is double taxation-profits are taxed at both business and personal levels. For most small businesses, attorney Sarah Barrack recommends pass-through entities like LLCs or S corps that provide liability protection without increasing tax burden.
Beyond incorporation, businesses often need state or city licenses, especially those involving safety concerns like food service, construction, or haircutting. Businesses serving alcohol or involving firearms face additional federal requirements. Protect intellectual property by researching existing patents and filing your own as needed. Choose unique business names and marketing materials to avoid infringement. Purchase appropriate insurance coverage including property and errors and omissions (E&O) insurance. Implement systems to protect customer data in compliance with regulations. Pay all taxes on time-payroll, sales, and quarterly estimated taxes-to avoid unnecessary penalties.
5장
Mastering Operations: The Engine of Your Business
Peter Stein transformed from an oyster enthusiast to a successful oyster farmer supplying New York's top restaurants in just five years. His success stems not just from delicious oysters but from meticulous attention to operations-from sourcing baby oysters to refining growth processes to marketing to restaurants. This operational focus is what turns thin margins into comfortable ones and determines whether a business becomes a fading hobby or a lasting enterprise.
Operations encompasses how your company transforms an idea into a finished product or service. Lisa Skluzacek from General Mills describes it as "process management"-figuring out how to get your product into customers' hands. This includes logistics, sourcing materials, inventory management, distribution, and sales processes. Small businesses often overlook these dynamics, but thinking about how jobs break down into component pieces is essential for growth and efficiency.
Whether you're working alone or leading dozens, observe and refine your work processes. Standardize routine tasks and document your system to easily identify problems. Gather actual data rather than relying on visual observations to make intelligent changes. Look for bottlenecks and trouble areas. Jonathan Sciabica discovered that changing his olive oil bottles from tall, thin designs to shorter, squarer models both streamlined shipping and made them more practical for consumers.
For product-based businesses, sourcing raw materials is critical. Peter Stein had to decide between leasing or buying bay bottom for his oyster farm, ultimately purchasing property from a departing farmer. He navigated extensive permitting processes with multiple government agencies without legal help, though he notes that depending on complexity, bringing in a lawyer might make sense.
Peter carefully evaluates oyster hatcheries based on size preferences, transportation costs, and performance tracking. He's used 5-6 different hatcheries over four years, continuously refining his choices based on value. Similarly, LaTonia Cokely of Adjourn Teahouse researches her supply chain through business networks to find herb sellers. She prefers buying directly from farms for sustainably sourced, organic options.
Managing inventory effectively is crucial. Peter expanded from three oyster hotels to about 130, housing around 2 million oysters that require regular inspection. Rather than building inventory software from scratch, he became a beta tester for existing software, recognizing that "80% accurate today is better than 100% accurate three months from now." His OysterTracker software helps balance supply and demand throughout seasonal growth cycles, allowing him to plan sales, staffing needs, and equipment purchases based on data rather than guesswork.
For distribution, Jonathan Sciabica revolutionized his olive oil business by using bag-in-box containers, which prevent oxidation for six months-solving a major product quality issue. After learning about this technology from UC Davis research, Jonathan found a manufacturer for the bags, had boxes made locally, and bought filling equipment. For distribution, businesses have various options: mail delivery (like Sciabica), delivery services for restaurants, private distributors for nationwide reach, or e-commerce platforms with drop-shipping.
Operations systems require constant refinement as technology evolves and customer demands change. Zellee faced challenges finding both manufacturing partners and raw materials like organic peach puree-supply chain disruptions are inevitable for any business. Some problems can be solved creatively, like LaTonia Cokely's strategy of offering "limited-edition" teas when certain ingredients are scarce. However, for critical supplies, Samantha Ku of Square advises developing backup plans: "Get very familiar with your supply chain. Identify what's normal for your business, what's within your control and what's outside your control. Prioritize the things that could actually close your business."
6장
Financial Foundations: Managing Money Like a Pro
Managing business finances requires careful planning. Stylist Germanee G built a $30,000 safety cushion before leaving her corporate job and now meticulously tracks finances through QuickBooks, operates from a home studio, and takes a modest monthly allowance. Her approach exemplifies the financial discipline needed for success.
Startup capital needs vary widely by business type. Research all legal requirements, including licenses and permits, before launching. Chef Leilani Baugh's experience of spending $1,200 on incorrect permits serves as a cautionary tale.
Plan for three financial categories: startup costs, personal expenses, and emergency reserves. Maintain six to nine months of operating costs, adjusting based on income volatility. Separate business and personal accounts for liability protection and accounting clarity. Ilana Wilensky of Jewel Branding uses distinct accounts for income, operations, client funds, and profits.
Establish a regular salary once income allows. "As soon as you're able, allocate money to pay yourself. Then schedule paying yourself-or you will always be the last priority," advises Ilana. Consider supplementing with quarterly or annual bonuses during profitable periods.
Consider hiring a bookkeeper when managing finances impedes revenue generation. When choosing a bank, prioritize low fees, online capabilities, and practical needs like cash deposit access. While online banks offer better digital tools, traditional banks may better serve cash-heavy businesses.
Build banking relationships early, maintaining regular activity for at least two years before seeking loans. Ensure cash flow is 4-5 times interest payments before taking on debt. Implement multiple payment methods and efficient invoicing systems to optimize cash flow.
Minimize payment risks by checking credit reports for large sales, establishing customer credit limits, and maintaining clear payment terms. Karen Turnquist advises that most unpaid invoices stem from miscommunicated terms rather than deliberate nonpayment. After three broken payment promises, suspend credit privileges - remember that sales only matter when paid.
7장
Building Your Brand: From Transactions to Relationships
Building a brand requires creating meaningful customer relationships and distinctive experiences. Courtney Foster, who transformed from high school dropout to successful salon owner, exemplifies this through her multi-platform marketing approach and constant focus on serving clients' needs through products, education, and engagement.
Business success hinges on relationships, not just transactions. Like the loyalty customers show to their favorite hairstylist despite occasional mistakes, businesses should cultivate trust-based bonds with customers. Ali Cudby, customer service expert, notes that 70% of purchasing decisions depend on how customers feel they're being treated-whether they feel "seen, heard, valued, and understood" during interactions.
Sales executive Joey Rault emphasizes creating distinctive customer experiences beyond the basic transaction. Successful businesses like Ben & Jerry's, Lululemon (hosting yoga classes), Barnes & Noble (offering cafes), and IKEA (showcasing furniture in homelike settings) create environments that invite engagement and make customers feel part of something special. Wild Rumpus bookstore in Minneapolis exemplifies this by incorporating cats, chickens, and hidden aquariums to create memorable experiences for children. Your business's personality must be authentic-not just marketing-starting from within and extending outward.
Word-of-mouth remains the most powerful marketing foundation, says Kathy Savitt, former Yahoo! executive. Start by introducing your business to people already connected to you-friends, family, colleagues-who appreciate your product's unique qualities. Offer samples or discounts to this core group, consider micro-influencers (10,000-50,000 followers) for affordable promotion, and actively solicit feedback to refine your offerings.
Understanding your audience is crucial before investing in broader marketing channels like social media, blogs, or advertisements. Without knowing what truly matters to your customers, expensive marketing efforts can be misguided. Focus first on refining your core business proposition through customer feedback, then expand your marketing reach.
When your existing network doesn't include your target audience, marketing partnerships can help generate buzz. Partner with complementary small businesses serving the same customer base-like a children's clothing store hosting your toy products as a limited-time offering. Beyond customer feedback, track referrals, purchase amounts, and frequency. Repeat customers signal a viable business ready for expansion through websites, emails, advertisements, social media, or loyalty programs that reward your most valuable customers.
A website is essential whether you sell online or not, as most prospects will research your business before buying. Your site should present basic information (name, logo, location, hours) while reflecting your business personality and telling your story. Andy Montgomery recommends investing in foundational brand design early-allocating $500-$2,000 for a logo, color palette, and typeface that can last for years.
To ensure potential customers find your website, implement search engine optimization (SEO). Sebastien Edgar recommends three key steps: use free keyword research tools to identify what potential customers are searching for, set up Google Search Console to track what searches lead to your site, and align your website copy with these findings.
Avoid generic stock photography in favor of authentic images. While hiring a professional photographer provides images you can use for years, you can take quality photos yourself with some guidance. Photographer Aundre Larrow advises ensuring photos reflect your brand personality and value proposition. For phone photography, use natural light (especially during golden hours after sunrise or before sunset), create depth by separating subject from background, and for food photography, use bounce cards to control lighting and smaller plates to keep proportions appealing.
Social media allows two-way communication with potential customers. Start by determining which platforms your audience uses, though maintaining some presence on Instagram, Facebook, and Twitter is advisable. Nick Dimichino recommends posting 3-5 times weekly with a consistent routine-perhaps products on Monday, employee spotlights on Wednesday, and community connections on Friday. Share promotions, behind-the-scenes content, and your founder's story to create engaging, shareable content.
While digital marketing is often the first choice for small businesses, traditional advertising channels can still be effective. Alana White, executive media director at Giant Spoon, recommends considering where your customers are and designing marketing to reach them there. Don't overlook community involvement-sponsoring local events or Little League teams can generate significant exposure at reasonable costs.
8장
Creating Your Dream Team: Hiring and Leading
Finding and managing the right team is crucial for business success. Restaurant owner Marc Bash prioritizes hiring positive, teachable people over experience, often recruiting through employee referrals. His approach has proven successful, with employees like a former non-English speaking busboy rising to management over two decades.
Leadership significantly impacts company success and culture. CEO coach Ron Beller emphasizes treating mistakes as learning opportunities and fostering open communication. Leaders should be specific about commitments and view "no" as a starting point for negotiation, not an end.
Self-care is essential for effective leadership. Google's Megan Jones Bell highlights how leaders' self-treatment affects their organization. She recommends mindfulness practices and creating purposeful transitions between work and home to maintain focus and calm.
Starting as a solo entrepreneur helps you understand your business thoroughly before expanding. The right time to hire comes when you're overworked, turning down opportunities, need specific skills, or can generate more revenue with additional staff. Heidi Schriefer of Grindr suggests hiring when you can make more money by adding staff and cover their costs.
Consider outsourcing personal tasks alongside business hiring. Services like childcare, housekeeping, or meal preparation can create valuable time refunds for business focus.
Before hiring, clearly define roles and expectations. Aaron Zamost recommends identifying what only you can do, then delegating other tasks. Start with detailed job descriptions, customizing them to your specific needs.
Many businesses begin with freelancers to manage costs and test different roles. This approach allows access to specialized talent without permanent payroll commitments and helps determine long-term hiring needs.
Diversity in the workplace drives better performance. According to McKinsey research, companies with high gender diversity were 25% more likely to have above-average profitability, while ethnic diversity showed a 36% advantage.
While technical skills matter, cultural fit is equally important. Your company culture - the guiding principles and working style - should align with your values and be intentionally shaped to support team success.
9장
Navigating Business Roadblocks and Pivoting to Success
When Letitia Hanke launched her roofing company, she signed contracts as "L.R. Hanke" to hide that she was both a woman and Black. Discrimination wasn't just a personal affront but threatened her business's survival. Early in her career, she experienced this firsthand when a couple who was enthusiastic over the phone gave her a glacial reception in person, ultimately rejecting her services with thinly veiled racism.
Every business faces challenges, whether discrimination or other obstacles like unexpected expenses, unreliable employees, changing consumer behaviors, world events, or new competition. Successful navigation requires being observant of trends and flexible in your approach. As Sarah Korpela of Luxury Estate Managers puts it: "It's not the survival of the fittest. It's the survival of the most adaptable."
When the pandemic hit in March 2020, Peter Stein's thriving business selling Little Peconic Bay oysters to New York restaurants collapsed overnight. Rather than panic, he pivoted to direct-to-consumer sales, leveraging his network to spread the word about home delivery. With help from a cousin who had developed school bus route optimization software, Peter created efficient delivery schedules. After surveying potential customers, he found overwhelming interest that translated directly into orders. Within the first month, he made 1,500-2,000 deliveries, and during one particularly intense week matched his pre-pandemic income.
When the pandemic hit, businesses had to quickly adapt to survive. Etsy sellers pivoted to making masks, generating $500 million in sales for a product with previously zero demand. Andrew Hypes, a DJ and music producer in Richmond, Virginia, found himself without work when clubs closed. Rather than giving up, he leveraged his Instagram following to advertise online music and production lessons, creating an adjacent revenue stream that sustained him through the first months of lockdown.
Jen Pratt of Fresh Sunshine Flowers in Sandpoint, Idaho built her business on delivering flowers anywhere in the area, but after three years, she was constantly stressed and frequently ill. She made the difficult decision to eliminate daily flower deliveries, which were time-consuming and unprofitable. Instead, she refocused on more meaningful and profitable services: weddings, floral subscriptions, and arrangements sold through a local grocery store. This strategic pivot allowed her to better plan her workload and income each month.
Diversification provides resilience during market disruptions. When the pandemic forced remote work, businesses needed to adapt by expanding online sales and geographical reach. Ilana Wilensky's company, Jewel Branding and Licensing in Atlanta, had wisely started a creative services division two years earlier, making them less reliant on any single income stream. During the pandemic, while clothing and accessories sales declined, their home products thrived.
When hairstylist Courtney Foster had to close her New York salon during the pandemic, she pivoted to virtual services. Recognizing many clients didn't even own basic hair tools, she created demonstration videos using her son as a model and offered virtual consultations where she coached clients and their partners through at-home hair care. Boyfriends cut hair and husbands applied relaxers under her Zoom guidance. Grateful clients often paid more than she charged.
After facing rejection based on her race, Letitia Hanke transformed her approach rather than giving up. She shredded the unsigned contract from the discriminatory couple and boldly rebranded her roofing company, prominently featuring her name and face on all marketing materials. Instead of hiding her identity, she made it central to her business. This transparency attracted customers in Northern California who specifically wanted to support a Black-owned, woman-owned business. The result was transformative-her company grew into a multimillion-dollar success story. Looking back, Letitia would thank those who challenged her: "They made me stronger. I have spent my whole life proving them wrong."
10장
From Survival to Scale: Strategic Growth
Leilani Baugh exemplifies ambitious entrepreneurship, having expanded from home cooking to running multiple restaurants, catering services, winery residencies, and pop-up events throughout the Bay Area. Starting in 2011 by selling dishes that combined her Chinese and Southern culinary heritage, she progressed to catering high-profile events, then opening Roux and Vine and the Magnolia Street Wine Lounge & Kitchen. Her vision extends to a cookbook, cooking show, and creating an incubator kitchen for women of color.
There's absolutely nothing wrong with running a business that stays about the same size if it pays your mortgage and gives you the flexibility you want. Valid reasons to stay small include: wanting to keep doing your current work rather than managing others; being the only one who can do your work (like an artist); avoiding the stress of a bigger operation; maintaining exclusivity in your business model; and prioritizing work-life balance. As Bobby Crocker of LVLUP Fitness says, "I work to live. I don't live to work."
"The number one thing every business owner wants to talk about is revenue and how to grow it," says sales executive Joey Rault. Growing revenue anchors business expansion, and there are multiple strategies to achieve this goal without necessarily changing your business structure.
Experimenting with pricing can boost your bottom line without increasing workload. Try offering discounts to see if you sell more; if sales remain constant, it suggests customers aren't price-sensitive. Similarly, test raising prices-if sales stay steady, keep the higher price. Direct conversations with top customers about pricing can provide valuable insights about what they value and how your prices compare to competitors.
Sometimes growth requires pushing beyond your comfort zone. DJ Andrew Hypes expanded his business by directly approaching decision-makers at clubs and bars, explaining who he was and why they should hire him. While initially uncomfortable, self-advocacy becomes easier with practice and is essential for business growth.
Physical expansion through new locations or larger spaces can increase your customer base. But online selling offers potentially exponential growth without time or location constraints. As Weebly founder David Rusenko notes, "Buyers are increasingly shopping wherever and whenever is convenient for them." The internet never closes, allowing you to make sales while you sleep.
Selling online requires more than just processing payments-you need systems to coordinate inventory across all sales channels. Platforms like Toast, Square, and Shopify can help manage inventory sold through multiple avenues. Streamlining sales channels by funneling customers to direct relationships rather than third-party marketplaces can simplify operations.
Expanding into related product lines can drive growth. Keith Miller added dog grooming to his dog daycare business when customers kept requesting it. Russ Kohler transformed his dairy farm into Heber Valley Milk & Artisan Cheese, distinguishing his business from competitors and increasing revenue by 800% over ten years by selling unique artisanal cheeses rather than just commodity milk.
Given a choice between new and repeat customers, repeat customers are always preferable. They cost five times less to retain than acquiring new customers, and are 3-12 times more likely to buy from you. Existing customers already know your work and don't have the hesitations new clients might have.
The Local Grocer sells CSA (community-supported agriculture) shares, a subscription model where customers pay upfront for weekly produce throughout the growing season. They've expanded from serving 40 families to partnering with two other farms to provide 26 weeks of food annually to 125 members. This benefits both sides-customers get guaranteed fresh food weekly, while farms can presell produce before planting, creating financial certainty.
Growing your business can mean letting others run it through licensing (others pay to manufacture products based on your intellectual property) or franchising (others pay fees and royalties to use your trademark, system, and ongoing support). Genevieve Weeks, a former ballet dancer with Oakland Ballet, created Tutu School for children in 2008. Starting in San Francisco during the recession, she found parents still spent on their children even in economic downturns. After systematizing operations and creating robust curriculum materials, she franchised the concept. Now there are 37 locations (34 franchises), with more opening soon.
11장
Planning Your Exit: Business Transitions and Legacy
After decades of running a business, knowing when and how to leave can be the hardest challenge. Harry Taub, a dentist of over forty years, couldn't simply close his practice-he had valuable equipment and patients he cared about. With no family members interested in taking over, he sold to a private equity firm while retaining partial ownership during the transition. This arrangement gave him more free time but less control, making it harder than expected to watch the business transform.
For entrepreneurs, planning your exit is as crucial as planning your start-especially since 80% of companies with revenues under $50 million never sell, and only 30% of family businesses survive to the second generation.
Creating a sellable business requires brutal honesty about your financial profile and whether someone else could successfully run your operation. Attractive acquisition targets share key qualities: they're profitable, have desirable assets, show strong future prospects, and offer something unique-whether it's innovative solutions, proprietary technology, unique customer lists, advantageous locations, or specialized equipment.
Family succession is rare but possible. As Michael Brown notes, "That option either exists or it doesn't." The two biggest challenges are founders struggling to let go and the next generation genuinely wanting the business. Acme Smoked Fish demonstrates successful multi-generational ownership, evolving from Harry Brownstein's 1906 door-to-door fish delivery into a global enterprise now run by his great-grandchildren. The current generation navigated complex equality issues by prioritizing family relationships over business tensions. "The reason we've made it this far is that we're family first," says Emily Caslow Gindi, co-owner.
Employee ownership transitions require three key elements: your willingness to step down, capable employees excited to take over, and a mutually agreeable price. Individual employee purchases are most common, typically involving someone in their forties or fifties securing an SBA loan to provide 90% cash upfront. Alternatively, Employee Stock Ownership Plans (ESOPs) work for businesses with at least 20 employees that can handle some debt.
Finding external buyers requires proactive research-identifying at least 50 potential purchasing companies, either independently or with professional help. Early consultation with investment bankers or attorneys specializing in small business sales is valuable, especially for first-time sellers.
Timing a sale requires aligning personal readiness (retirement plans, health concerns, stress levels) with favorable economic conditions. Even thriving businesses face challenges selling during unfavorable interest rates or industry downturns.
Ironically, the best time to sell is when prospects remain bright-exactly what attracts buyers willing to pay premium prices. Be flexible with timing; if a good buyer appears before your planned exit, consider adjusting your timeline.
Maintain full operational focus right through the sale process. Potential buyers want a business running at peak performance, not one showing signs of neglect. Resist cutting corners on investments, as this directly impacts offers received. Remember that buyers may want you to remain for 2-5 years post-sale to ensure smooth transition.
Prepare for sale by meticulously organizing documentation. "You need at least three and ideally five years of clean, clear, professionally organized records," advises Brown. Separate personal expenses from business accounts, build teams and processes that can function without you, secure long-term contracts with key employees, and document all verbal agreements.
If selling proves impossible, simply closing may be cleaner than forcing an unsuitable transition. Financial planner Judith McGee recommends diversifying wealth beyond your business: "Under-live your income, take distributions, and keep your debt down." Another option: hire someone to run daily operations while maintaining ownership-this demonstrates the business can succeed without you while creating future sale opportunities. "It buys back your time and makes your company super salable," notes Brown.
