A while back, my wife and I became part owners in a local coffee shop.  I’m glad I did this because these experiences have taught me a lot about what early-stage entrepreneurs face.  While I have degrees in accounting and have been serving entrepreneurs for a while now, it’s my experience of actually being in a growing business that has given me a new-found respect for what start-ups deal with.  After reflecting on these experiences, I’d like to share my sense of the top ten challenges for boot-strap entrepreneurs and some ideas to address these challenges.

Serial entrepreneurs love to start and grow companies, up to a certain point.  But then they often lose interest and go looking for some new exciting business opportunity.  Many times, the businesses they’ve already started are just beginning to thrive as the entrepreneur’s interest wanes.  But the future of those companies is far from certain.  The risk to serial entrepreneurs is that they’ll put their family’s long-term financial health at-risk if they start a new business before their current businesses are ready to thrive without their full attention.  If you’re thinking about starting a new business, even though you already have one or more businesses, I recommend that you do these seven things first.

Over the last few years, I’ve had the privilege of working with SMB (small-to-medium business) contractors.  Many of these companies are family businesses where a founder established and grew the business.  Most of these companies have been around for at least a decade and have provided a good income and even a sense of identity to the family.  But sometimes, an independent valuation of the business shocks the owners with a sense of disbelief.  If you or someone you care about has faced this situation, here are five strategies that can really help you.

Attracting new talent is challenging for everyone, it seems.  In the past, organizations relied on referral networks, job boards, recruiters or even word of mouth.  But in today’s hyper-competitive climate, many of these strategies no longer work to the satisfaction of the entrepreneurs we serve.  So, what does work?  Over the last couple of years, we have been implementing some strategies that are really paying off for us.  Let me share, for your consideration, seven principles that could really help you compete and win in today’s job market.

Over the last several years I’ve had the privilege of working with numerous entrepreneurs on their estate plans.  While no one wants to think about their demise, entrepreneurs often have complex financial lives and sorting through the details and making decisions requires a lot of time and energy.  If there is one thing I’ve learned, it’s that putting things off to a future date only makes the situation more challenging later.  If you need an estate plan, or if you need to update your old estate plan, here are my top 5 considerations to help you build a plan that realizes your dreams.

I love working with SMB contractors and real estate investors.  These fiercely independent entrepreneurs take great pride in not relying on traditional financing solutions and bootstrapping their own ventures.  They possess a strong work-ethic, are family-oriented and chart their own course in life.  Most of them are self-made.  But this independent mindset is both a strength and a weakness.  I find that SMB contractors and real estate investors often do not seek advice when they should.  The result is that they usually end up paying far more in taxes than they had to.  The solution to this problem is active tax planning.  I’d like to share with you 5 reasons SMB contractors and real estate investors really need active tax planning and how this strengthens their family’s financial standing.

Over the years we’ve helped several clients vet the formation of off-shore business partnerships.  These business relationships allow our clients to achieve scale, move up-market and do work that is often not available to be done in the US or that can only be done at a financial loss.  However, these relationships can be tricky to form.  After reflecting on the situations I’ve seen our clients encounter and even our own experiences, I’d like to put forward five questions that I think will help you assess your situation.

Over the last few years of working with entrepreneurs, something has become quite clear to me.  Our clients need more than just great tax advice, tax strategies and clean tax returns.  If we help our clients save thousands of dollars on taxes but that money does not improve their overall financial standing, what have we really accomplished?   The people we are so fortunate to serve are passionate and hard-working.  They have big dreams, both for their business and their loved ones.  It takes money to make those dreams come true.  It takes a great financial plan.

I began my career in public accounting 55 years ago.  Over that period of time, I’ve served thousands of clients, many of whom are entrepreneurs.  As I reflect on the last 50+ years, I have begun to crystalize, in my own mind, what the entrepreneur of the future will need from their CPA.  When I look ahead to the next 50 years, based on how much things have changed over my career, I believe entrepreneurs should look for these five traits from their CPA.

Entrepreneurs know that the US economy goes through cycles. Things have been steadily improving since early 2010. Are we entering a down-cycle? I cannot predict the future and don’t believe that anyone can. But after many years of working with and for entrepreneurs, I have come to believe that you can survive a downturn and potentially even thrive through it or rebound quickly after it ends. Here are 5 key strategies to help you do this.

Recently I’ve been working with growth-oriented entrepreneurs who are trying to make an important decision.  They are grappling with the need to grow, but are unsure whether to buy a business or to invest in their current business.  This decision could be make-or-break for them so it’s important to get it right.

The new tax laws have produced both excitement and anxiety.  Entrepreneurs in particular have the opportunity to benefit from a reduced tax burden, but this introduces another challenge.  What do you do with the money you save on taxes?  It’s a good problem to have, but it’s still a problem.

I believe that to thrive in the new economy you have to give yourself space to anticipate and act with boldness. I think of this as anticipatory resilience. This is about avoiding the blow, not recovering from it. After working with dozens of entrepreneurs and helping them navigate their ups and downs, here are my lessons learned about how to thrive through disruption.

For most businesses, it’s nearly impossible to scale the company and achieve meaningful growth without also scaling human resources. Many of our clients face this challenge. Human capital can be the single biggest factor holding them back from achieving their growth goals. For the last 20 years, I’ve tackled this problem day after day and I’ve learned a lot of lessons about what works. I’d like to share them with you.

Over the last few years, I’ve had the great privilege of working with successful entrepreneurs.  I’ve also watched people launch businesses and then struggle.  Starting a new business is a risky venture.  Sometimes it can feel as if there are secrets successful entrepreneurs know that the rest of us don’t know.  That can be frustrating.  After serving hundreds of entrepreneurs, I’ve come to recognize five key areas that tend to accelerate early-stage success.  Here are my lessons learned.

The new tax law was recently passed to great fanfare.  It has been billed as the biggest tax break Americans have seen in decades.  While this may be true, especially for people with ownership interests in one or more businesses, discovering how to realize these tax breaks is a whole new ballgame.

In December 2017, Congress passed the most significant tax reform bill in thirty years.  Some of the provisions were designed to simplify tax reporting, but some of the provisions have made tax reporting significantly more complicated.  One of the more complex areas is the new deduction for “qualified business income” – often referred to as QBI.  This new provision should provide a substantial tax benefit to individuals with qualified business income from a partnership, S corporation, LLC, or sole proprietorship.  But it may not be as straight-forward as it seems at first glance.

Congress has passed the biggest tax reform bill in thirty years. These new tax laws will make fundamental changes in the way you, your family and your business calculate your federal income tax bill. They will also likely change the amount of federal tax you will pay.

Most entrepreneurs I work with are busy people who are confronted with more decisions than they have time or the desire to research.  The implications of making the wrong decision or of not fully executing on the right decision can be severe.

Investors who play the markets are often torn between fear and greed.  When stocks go up, they buy, sometimes taking on more risk than is wise.  When stocks go down, they sell, usually out of concern for losing it all.  Typically these investors follow trends because they fear they are missing out on opportunities.  Fear and greed.  These two shape the mindset and behavior of a certain type of investor.

My uncle is a successful construction industry entrepreneur who today owns 5 businesses. Nothing in his early life suggested that he would accomplish so much. He came from a challenging childhood environment; his family was not wealthy; he did not grow up in a family business; and he did not complete high school.

When most people think of CPAs, they probably picture a technician who is very good with numbers. CPAs are often thought of as being left-brained dominant. They are analytical, good with numbers and “just-the-hard-facts” kind of people. Right-brained people are thought of as creative. They are good at language, art, abstract ideas – you know – the softer mushier stuff of life.

I’d like to address a common concern I hear when talking to people about CPAs.  While they like their CPA and believe they’re competent, they wish their CPA was more proactive.  Usually what they mean is that they want a CPA who is looking out for them and their business interests.  They either feel that not enough time was spent getting to know their issues or that an issue came up during a conversation or meeting that should have been addressed long ago.

In the twelve years now that I’ve been with Casey Neilon, we’ve had the privilege of serving dozens of entrepreneurs who are going global.  You may not think of Casey Neilon this way, but we are trusted advisors to business owners with international aspirations and operations.  After working with numerous entrepreneurs, I’ve come to recognize just how feasible and how valuable this move can be.  It is probably more doable than you might realize.  But there are also many pitfalls to avoid.  Here are six key considerations for entrepreneurs who want to expand globally.