Business and tax strategies change as a company grows. In this episode of Real Talk for Resilient Owners, Kim Gaxiola talks with business partner Carolyn Rowland, a CFP® and Enrolled Agent, about proactive tax planning—from choosing an entity structure to preparing for a future business sale. They discuss why tax planning should happen throughout the year, not just at filing time, and how owners can evaluate opportunities while staying compliant. The conversation also covers the trade-offs of an SCorp election, retirement plan options, pass-through entity tax elections, and why succession planning should start earlier than many owners expect.

• In this episode they cover: The difference between tax filing and proactive tax planning
• When an LLC taxed as an S Corp may be worthconsidering—and the extra responsibilities it brings
• How an S Corp election can affect payroll, Social Security contributions, and retirement planning
• Ways a 401(k) or profit-sharing plan may support retirement savings and tax planning
• How pass-through entity tax elections may help some owners manage state and local tax deductions
• Why the best business structure for growth may not be the best structure for a future sale
• How to plan backward from a business owner’s succession or exit goals
• Why early planning and regular check-ins matter as the business evolves
• The value of coordinating tax and financial planning

Key Takeaways

• Tax planning is most useful when it happens before year-end, while there is still time to consider options.

• An S Corp election can bring potential tax benefits, but it also adds payroll and compliance responsibilities. The right timing depends on the business and owner.
• Retirement plans can be part of a broader tax and financial strategy.
• Business owners should review their entity structure as their business changes.
• Succession and exit planning can influence decisions made years before a sale.

Visit ⁠http://www.resilientplanning.com⁠ to learn more about our team or visit https://www.resilientplanning.com/start-todayto schedule some time with our team.

Show Notes

• Business Exit and Succession Planning-CLICK HERE
• Resilient Wealth Planning YouTube Channel- CLICK HERE
• Have a question? Send an email to hello@resilientplanning.com

In this episode of Real Talk for Resilient Owners, Kim Gaxiola speaks with Jay Shergill, president and founder of Virtual Admins, about how small business owners can scale withoutgetting buried in admin work. They discuss offshore staffing, data security, task audits, and where AI fits in as a support tool rather than a replacement for people. Jay explains how he built his own business by delegating work, then turned that experience into a staffing solution for other owners who need leverage, not more busywork.

Key Topics

• Jay Shergill shares how he started Virtual Admins in 2019 after building his own solo accounting and bookkeeping business.
• The conversation centers on why offshore staffing is not just for large companies, but also for solo entrepreneurs and small businesses around the 200K level and below.
• Jay explains that the goal of outsourcing is not to replace in-house staff, but to support business growth by removing low-value tasks from the owner’s plate.
• Data security is a major concern, and Jay outlines practical checks like firewalls, USB blockers, website blockers, secure work environments, ISO certifications, NDAs, background checks, and strict password access controls.
• He strongly advises owners never to share master. passwords or broad software access, and instead create separate users with limited permissions.
• Jay describes moving his team from home-based work to a corporate office in India in 2023 to improve accountability, reliability, response time, and security.
• Kim and Jay discuss how often owners should audit their tasks, with Jay recommending monthly task reviews and quarterly deeper audits to identify what should be delegated.
• Jay shares how he personally shifted from spending most of his time on emails, invoicing, CRM updates, and collections to focusing on networking, client conversations, and growth.
• The discussion highlights the dangers of owner burnout, revenue leaks, missed appointments, and late follow-ups when business leaders try to do everything themselves.
• Jay explains why AI should be treated as a tool supervised by humans, not a substitute for human judgment, trust, or emotional intelligence.
• The episode closes with a reminder that workflows and systems make delegation easier and increase business value, especially for succession planning.

Visit ⁠http://www.resilientplanning.com⁠ to learn more about our team or visit https://www.resilientplanning.com/start-today to schedule some time with our team.

Show Notes

• Connect with Jay Shergill via LinkedIn- CLICKHERE
• Virtual Admins Website- CLICK HERE
• Resilient Wealth Planning YouTube Channel- CLICK HERE
• Have a question? Send an email to hello@resilientplanning.com

In this episode of Real Talk for Resilient Owners, Kim Gaxiolasits down with Shailendra Gupta, President of Trans World Business Advisors of Fremont, to unpack what business owners need to know about valuation, mergers and acquisitions, and selling a business the smart way. Shailendra explains whyso many owners underestimate the value of their business, how the sale process really works, and what can make or break a deal. From reducing owner dependency to cleaning up financials and planning early, this conversation is full of practical advice for owners thinking about an exit.

What You’ll Learn

• How business valuation actually works
• Why many owners leave money on the table
• The biggest mistakes that hurt a sale
• How to prepare years in advance for an exit
• Why family businesses and partner-owned businesses can get complicated
• What due diligence looks like from the buyer’s side

Key Takeaways

• Many business owners don’t realize their business has value until they get an outside valuation.
• Clean financial records make a business more credible and easier to sell.
• A business that depends too heavily on the owner is harder to transfer.

• Customer concentration and legal issues can reduce value significantly.

• The earlier an owner starts planning, the more options they’ll have.

Subscribe now to stay updated on future episodes and join us on this journey to financial empowerment.

Visit ⁠http://www.resilientplanning.com⁠ to learn more about our team or visit https://www.resilientplanning.com/start-today to schedule some time with our team.

Show Notes

• Shailendra Gupta Contact Information- CLICK HERE
• Resilient Wealth Planning YouTube Channel- CLICK HERE
• Have a question? Send an email to hello@resilientplanning.com

Key Takeaways