No. 8

5 Lessons From a Thriving Doggy Daycare Entrepreneur

5 Lessons From a Thriving Doggy Daycare Entrepreneur
Dillion Toscano, Chief Executive Officer of deluxe pet boarding shop Wags 2 Whiskers in Culver City, California knows firsthand how to navigate change, uncertainty, and disruption. He shares the lessons they learned along the way.
by Aja Evans, Keila Hill-Trawick Sep 28, 2023 — 5 min read
5 Lessons From a Thriving Doggy Daycare Entrepreneur

About this series



Discover the more surprising sides of your business finances. From unique seller spotlights (did anybody say taxidermy?) on tackling cash flow to monthly advice from a Financial Therapist and CPA — check out these stories and more from our banking newsletter.
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Please note that the author of this article is not an employee or consultant of Square. The information they provide in this article solely reflects their views and is not endorsed by Square. This article is for educational purposes and does not constitute legal, financial, or tax advice. For specific advice applicable to your business, please contact a professional.

“I’m not a business person,” says Wags 2 Whiskers Chief Executive Officer Dillion Toscano. At the same time, the owner of the deluxe pet boarding shop in Culver City, California, knows that navigating change, uncertainty, and disruption are some of the most important skills an entrepreneur can have.

After all, Toscano, who runs Wags 2 Whiskers with his wife, expanded a business dependent on people leaving their homes through the COVID-19 pandemic. At the time, they didn’t know if they were going to be forced to close, so they created a new game plan.

Today, they are thriving. Toscano shares the strategies Wags 2 Whiskers employed to overcome obstacles and create new opportunities for more revenue in their business.

Use all your available resources.

Toscano isn’t a traditional businessman, so he didn’t use traditional banking systems. Apart from government loans, he took advantage of Square Loans. “I don’t know how I would have been able to make the decisions I made without having [Square Banking] resources, which made it clear to me how much money I could spend to improve the business.” With the combined funding of government loans and Square Loans, he modernized Wags 2 Whiskers’ business operations and updated their customer relationship management systems and social media accounts so they could reach out to customers during critical times.

Find the silver lining.

Toscano says they initially lost a lot of business during COVID’s early days because everyone was able to keep their dogs at home. Then they realized they could use the downtime to invest in improving their facilities, like using their loan from Square to purchase a $10,000 water distiller. “We invested in technology such as a water distiller system and an earthing floor system for the dogs … and we were able to build the business even better.” These improvements enhanced the overall experience of their furry clients, and set Wags 2 Whiskers apart as a one-of-a-kind, green, holistic pet-care service. “Today, it’s our unique selling point,” he explains. Offering specialty services has helped them thrive — and has kept their customers coming back.

Have faith and trust the flow.

Toscano also stressed the importance of faith and prayer in his journey. “I prayed a lot,” he says. Opening his mind to divine knowledge allowed him to tap into his intuition. “If I were to try to control what was happening during the pandemic, I would have closed my business because I wasn’t earning enough money to stay open.” Instead, he let go of the need to control everything and trusted in the flow of life, which led to unexpected opportunities and solutions, like leaning into holistic care for his four-legged clients.

Recognize your value.

Toscano says the pandemic taught them to recognize the value of their services and charge higher prices if needed. “[We realized we] had a loyal following that was willing to pay for the quality and value we offered, and that the next step was really to have faith in yourself and ask for that value.” Despite raising their rates, Wags 2 Whiskers customers remained loyal because they believed in the importance of Toscano’s services.

Center your business decisions on your values.

Toscano was able to make bold moves during an uncertain time because he knew the pandemic wasn’t going to last forever, leading Wags 2 Whiskers to find other opportunities to grow. He also made sure he stayed true to what he valued: caring for pets in a holistic and sustainable way.

Carlo Carrascoso, professor of business and director of the Banta Center for Ethical and Purposeful Leadership at the University of Redlands, says keeping your values at the center of business decisions can help navigate hard times. “There’s not a separation between being a good business person or being a good person,” says Carrascoso. During unpredictable times, identify and weigh your obligations to all stakeholders — from family to employees and customers — to ensure you’re making the fairest decisions overall. “Good ethics is good business, because if people know they can trust you and that you look out for them, you’re creating a virtuous circle that actually promotes the business and increases your profits.”

And Toscano’s bold moves paid off: He just got awarded the ability to franchise Wags 2 Whiskers. Toscano remarks, “[With] all those bells and whistles — the high-quality water, earthing floors, and green cleaning — we created a package that appealed to potential franchisees so we can grow our brand.”


of Square Loans sellers use their loan for new equipment, according to a survey of 1,001 sellers who accepted a loan from Square (January 2023).

Finance in focus: Bite-sized steps for better financial literacy.


Aja Evans is a Licensed mental health counselor who specializes in Ffnancial therapy. She owns and operates a private practice in New York City. 

How much do you think you know about money? Chances are you know more than you give yourself credit for. 

Financial knowledge is essential for long-term business success. Without it, our emotional mind has the power to hijack our decisions and lead us down a road of poor choices and financial mismanagement. Understanding key concepts like P&L sheets, budgets, taxes, and general money management can enable you to do what is best for your business. 

This month, pick one concept, like the P&L sheet, that you want to learn more about. Commit to learning more about it over the next 30 days — listen to a podcast, get P&L tips from a business owner friend, or fill in a profit and loss template.

Learning about money isn’t just for the financial experts. It can help you improve and evolve as a business owner, so you and your business stay flexible to meet ever-changing market demands. The more you make financial education a habit, the more confident you’ll feel about the decisions you’re making for your business.

Good With Numbers: Want to make smarter business decisions? Look to your taxes.


Keila Hill-Trawick is founder and CEO of Little Fish Accounting, a boutique CPA firm dedicated to serving micro-businesses through accounting and tax support.

Everyone hates taxes. But what I have found is that the stress of taxes comes from a lack of organization, more so than a misunderstanding of the tax code.

Your tax liability is directly tied to your income and expenses, so proper maintenance and organization is the key to being prepared.

When you file taxes in April, you’re actually filing for income and expenses that occurred as of December 31 of the year before. That means the real work is done throughout the year, not only when you file your return — taxes are year-round. 

They can also have a significant impact on how you structure your pricing. The goal is for your pricing to cover all your operating expenses, including taxes. For example, if you charge a client $1,000 but the total taxes end up being $250, you didn’t actually make $1,000. You should’ve actually charged closer to $1,300 to clear $1,000 in revenue.

But to understand what’s needed to prepare, you first have to understand how taxes work. Get a detailed breakdown of what your taxes are telling you and how to use them to make more strategic business decisions in this 16-minute podcast episode.  

All loans are issued by Square Financial Services, Inc., a Utah-Chartered Industrial Bank. Member FDIC. Actual fee depends upon payment card processing history, loan amount, and other eligibility factors. A minimum payment is required and you must repay your loan as specified in the loan terms. Loan eligibility is not guaranteed. All loans are subject to credit approval.

Aja Evans
Aja Evans, a Licensed Mental Health Counselor who specializes in Financial Therapy. She owns and operates a private practice in New York City.
Keila Hill-Trawick
Keila Hill-Trawick is the Founder and CEO of Little Fish Accounting, a boutique CPA firm dedicated to serving micro businesses through accounting and tax support. Based out of Washington, D.C. by way of Atlanta, GA, Little Fish serves clients nationwide.

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