basketball court

Hiring an Entire Person

Imagine you’re the coach of a winning basketball team. You’re doing pretty well but, you’ve lost a few games that you feel could have been won if your players hadn’t been out-rebounded. When it’s time to start scouting for the next season, you find yourself trying to decide between two players.

basketball players reachingThe first player is built like Shaq (the younger, leaner Shaq) and is a rebounding machine. Unfortunately, he shoots like Shaq at the free throw line (only from the field as well), slacks off on defense, and is rumored to be a diva in the locker room.

The second player is a great all-around recruit who has high stats in points, assists, AND steals, and is known to be a hard worker and generally well-liked guy. The only downside is that he’s built like Muggsy Bogues, and, unless you’re playing an exhibition game against a preschool team, is not likely to be pulling down any boards.

So, who do you draft? If you’re like me, you take the second player every time. It works this way in business too. You may find an area in which you feel your team is currently lacking and try to recruit to fill that specific gap. But that’s not always the best choice.

man makes basketball goalFirst, let’s discuss the reasons why you shouldn’t hire someone just to fills a skills gap. For starters, you may not need enough help in that particular area to fill an employee’s time. In a basketball game, there’s a lot more a player needs to do than just stand around under the goal, boxing out to get rebounds.

Or it could be that there’s too much of a need in one area, and one person can’t do it alone. Even if someone is the best rebounder in the world, if they’re the only one from their team under the net facing down five other guys, their chances of success go way down.

Finally, particularly in certain high-demand positions, an individual with a specialized skillset might not be the best fit for the team overall. They could bring an ego or simply have a personality that does not work well with your company culture. (Or they could be so lacking in other areas as to be a net drain on productivity.) In those cases, another player is a better option.

women reach for basketballSo now, let’s discuss how you can fill skills gaps in your company without making it a hyperfocus of your hiring. For starters, look at how you can train and improve the staff you already have. Rebounding stats go up when the entire team is fighting for position and going for the ball, even if no individual is a rebounding superstar.

Second, look at how other areas in which you’re stronger can be used to supplement the area of perceived weakness. To continue with our analogy, a team that struggles with offensive rebounding need not struggle so much if they improve their field goal percentage and make more of their shots on the first try.

Finally, remember that you cannot hire only part of a person; you have to take all of them, the good and the bad. Look for someone you are excited to have around for the long-term, who not only has a skillset that can be immediately useful, but for someone who can grow and develop within your company to become an indispensable MVP.

falling man

Facing Your Fears, at Your Pace

Entrepreneurs like to embrace an aura of fearlessness. However, humans possess the ability to fear because it is a useful emotion. Fear helped us avoid lightning, and sabretooth tigers, and that same instinct exists within us today, and can help us avoid modern dangers (like human predators).

The problem comes when the fear instinct attaches itself to something which cannot literally hurt us, but which may "only" carry the risk of psychological harm. (Even then, the harm is likely overstated in our minds.)

sad man with head in handsThe instinct may exhibit itself as a fear of public speaking, or firing an employee, or submitting a sales proposal. These are all things that, in general, entrepreneurs need to be able to do. We need to be able to talk to strangers, or rid ourselves of problem staff, or ask clients to hire us. These things are necessary for the well-being of our business. Our fear instinct is actively working against our financial survival.

Of course, being entrepreneurs and, by nature, often people of extremes, our subculture has encouraged us to take a disproportionate response. We are told to "live fearlessly" and to "step outside our comfort zone". The narrative envisions the wallflower inventor wiping off their sweaty palms, calming their shaking voice, and pitching in front of the "Shark Tank" investors for millions of dollars.

sad face drawingI believe that our comfort zone exists for a reason. Often, within our comfort zone is where we work best and most efficiently, and it should be where we spend the majority of our workday: doing what we do best, and what we're comfortable with. The comfort zone is only a problem when it is restricting.

My proposal then is that, instead of leaving our comfort zone, we expand it.

Visualize your comfort zone not as a chalk-lined circle which you can easily step out of via sheer will, but as a protective bubble. If you gently push the walls of that bubble, you can stretch it in any direction which you choose, while still remaining safely inside.

woman giving presentationFor practical purposes, this means, for example, starting with a Toastmasters Club visit before you agree to speak in front of a large auditorium. If you've never had the displeasure of leading a termination meeting with a non-performing staff member, start with leading employee performance reviews. Practice your sales proposal on a friend before you present it to a prospective client.

Don't feel pressured to be "fearless"; just start making yourself more comfortable with small steps. You'll still reach your goal, but will avoid the pain and risks which your fear exists to protect you from.

mother and father and two sons holding hands walking

When You’re too Small for FMLA

Per the US Department of Labor, “The Family and Medical Leave Act (FMLA) provides certain employees with up to 12 weeks of unpaid, job-protected leave per year. It also requires that their group health benefits be maintained during the leave…FMLA applies to all public agencies, all public and private elementary and secondary schools, and companies with 50 or more employees.”

Of course, most of us in the small business world, by definition, have less than 50 employees. However, we still have employees who get sick, or have kids, or have other reasons for which they need to take family and medical leave. And most employers (who are good employers), want to find a way to take care of their most valuable asset – their employees – even if it’s not strictly mandated by federal law.

So, business owners are left with a balancing act, to protect their staff and keep them happy, but to not cost too much in money and productivity. To assist, we have put together this list of FLMA alternatives which small businesses might utilize.

mother crouching to look at son with a smilePaid Time Off

This is the easiest, as it’s something many businesses already have in place. Instead of designating what time off might be used for, have a clear policy (in writing), that describes how PTO is earned, how much each employee receives, and how much notice is required (if possible) for it to be put into use. Some employers like to separate “sick leave”, “vacation leave”, “personal leave”, etc. However, requiring proof, such as a doctor’s note, that leave used was sick leave is tricky, and can get into privacy issues. Also, there might be other, very personal things, for which a person might need to use leave and would not want to provide a note (a court hearing for an adoption, or fertility treatments). Having a generous PTO policy is easier to track, and allows employees the freedom to use time off as they see fit.

alarm clockFlex Hours

Obviously, certain industries do not lend themselves well to flex time. (It would be hard to staff a restaurant or construction site where anyone could come and go as they please without notice.) However, in certain businesses, where the majority of the day is not customer-facing and communication typically occurs via email (i.e. programming), it can be helpful to let staff set their own schedule. This way, they can leave for appointments without as great a loss of productivity. However, it is important that team members still be considerate of each other and, for purposes of connecting and collaboration, keep each other apprised of when they will be in-office or available.

sitting on bed working on laptopWork-From-Home

Working from home temporarily or part-time can be a great way to keep an employee who needs time away for medical or family leave somewhat connected with the office. This way, they do not suffer the loss of income associated with a lengthy leave, and the business does not suffer the loss of productivity which comes with having a key person completely unavailable.

doctor writing on a clipboardFMLA Compliance

All FLMA really means is that you keep an employee’s position open while they are out on extended leave. Even if you are not large enough to be legally required to do so, it’s not a bad idea. The gap can be filled with temporary help and, in fact, using a temp-to-hire person can be a great way to fill in (in case your employee chooses not to come back from leave).


Having an employee need to take substantial time away from work can be stressful on everyone. However, flexibility and collaboration can ensure that your business needs are covered, and that your employees feel secure in their position with you. Whatever your plan, be sure to have it documented in writing, and reviewed by an employment attorney or HR specialist.

sparkler in front of american flag

Rebellion vs. Revolution

My favorite retelling of the Revolutionary War comes from the musical “Hamilton”. In it, the titular main character bravely fights for independence, but also muses about what freedom will mean for the colonies, and how they will structure their country and face their economic woes. After serving under General Washington, he goes on to become the first Secretary of the Treasury and to put into place systems and structures which are still integral parts of our government today.

I believe that this can parallel the experience many people go through when they leave employment to found their own companies. There are those who fight valiantly for independence, but fail to plan for a replacement system. There are others who are more cautious and plan so carefully that they never take that first step to leave the security of their current situation. (You could say they “throw away their shot”.) Success is found by those who can both dare to leave the harbor, but who also know where they’re sailing.

Rebellion vs. Revolution

american flagThe word “rebellion” brings to mind images of sullen teenagers, instinctively acting out against their status quo. For a disgruntled employee dreaming of business ownership, it can be chafing against inane workplace rules, or simply longing to leave the 9 to 5. However, it’s not enough to know you are displeased with your current situation; you have to have a vision of what you want to replace it with.

We’ve met plenty of people whom have a lofty dream of how they envision business ownership. (For some disastrous examples, see our article “Living a Lie: The Mistakes that Make Entrepreneurs Go Broke”.) We even had one would-be business owner tell us, “Oh, I don’t want to work. I’m going to hire other people to do the work, and then I’ll just travel or something.” Needless to say, that plan didn’t work out.

statue of libertyThe successful businesses are those whose owners have the spirit of revolution. It’s not just that they’re unhappy with their lot, but they clearly see how it, and their own small slice of their particular industry, could be better. These are the people who desire to “build a better mousetrap” with their company, and who aren’t afraid to put in the work to do so. We have successful clients who have invented new products or medical processes, but we also have those who have succeeded by coming up with ideas for local entertainment, or who have simply found a way to be the most effective attorney, or marketer, or even HVAC person in their field. And none of them are afraid of work; in fact, the most successful all embody attitudes of continuous improvement, both in themselves and in their companies.

If this 4th of July you find yourself pondering the plunge toward business ownership, examine where that desire is coming from. If you’re ready to start a revolution in your industry and in your life, build a plan for where you hope that path takes you, and a vision of what it looks like when you’ll get there.


I guess this is growing up.

I always find the end of May a bittersweet period, with its focus on graduations and plans for the fleeting summer. It's a time of celebrating the crossing of an arbitrary boundary we have created between "child" and "grown-up". And, with The Bookkeeper having just celebrated our sixth year in March, I've been thinking a lot about what growing up means for a company.

What I've found is that, much like how many adults will confess to still really not feeling like grown-ups, I think it's hard to pin down exactly what being "grown up" means for a company. However, there are a few things I keep coming back to.

1. You know who you are.

business woman shaking handsFor most teens, a major source of anxiety is whether or not people like them. Often they are either chasing popularity, or trying to conspicuously prove they don't want it. Many new business owners start the same way. In the interest of making connections and gaining customers, they try to be everything to everyone. But comfort and maturity comes with knowing the work you like doing, what you do well, and focusing on being the best you can at that.



2. You choose who you surround yourself with.

man and woman talking on sidewalkWhen you're younger, your friendships, though dear, form generally through default. Your best friends are the kids in your class or neighborhood, or with whom you play on a team or share some activity. When you first start a company and enter the social world of small business, you run into the same people over-and-over at networking functions, morning meetings, etc. Over time, you identify which of those people with whom you feel a real connection, and develop some great friendships. But at the beginning, you'll make a lot of coffee appointments with people who don't have your best interests at heart. Sometimes you'll even know that going into the meeting, but you'll feel too "new" to shoot anyone down. As you grow up, you learn to recognize the people with whom you want to spend your precious time, and you won't feel hesitant to prioritize your calendar accordingly.


3. You're unashamed to let your childish side show.

child with finger paint on handsYoung people go through a period where they are ashamed to play and then, at some point in adulthood (if they're lucky), they rediscover the joy in acting like a kid. In your business, it's important to keep that playful joy and remember why you love working for yourself. (We didn't escape corporate to create corporate.) This doesn't mean being reckless or irresponsible; it just means letting go enough to embrace the fun that comes with being a business owner. This can be something as simple as realizing it's a beautiful day and you've got no afternoon meetings, so you leave the office to hit a few miles of trail (me). Or, it can be something as big as taking your entire team and all their families to the beach for a weekend (Craig). The point is that, without falling into the trap of anything as contrived as "team-building", you find ways to enjoy the work, and the flexibility the work gives you.

Of course, just like a graduating high school senior who thinks they're grown, I might have no idea what I'm talking about. When The Bookkeeper is 10 years old, or 20 years old, or, should I live to see it, 50 years old, I might look back and laugh at my own youthful naivete. All I can do for now is look forward to what I'll know then.

company meeting table

Three Lessons From Last Year

The end of the year is a time for reflection.

However, if you’re in the accounting profession, there’s little time to reflect at the actual end of the year, as January is our busiest month. So, the end of January becomes your default time for reflection.

As we approach the company’s six-year anniversary, it’s easy to look back on the things we’ve done over the last few years. From a family business operating over the kitchen table, with only a handful of clients, we’ve grown to a team of eleven full-time staff serving over 170 clients. We’ve met a lot of people and helped a lot of businesses but, more than what we’ve done, I’ve been thinking about what we’ve learned.

I could (and someday might) write a book about what I’ve learned through small business ownership, but today I wanted to talk about three lessons that have stood out to me from the past year.

Celebrate wins, but keep training in the offseason.

celebrating office workersFinishing a big project, landing a big account, or getting kudos from a client is a great high. It’s a time to recognize staff, and give yourself a pat on the back. But it isn’t the time to stop what you’ve been doing.

When things are going well, it’s easy to get complacent. But it’s effort that breeds success, and that can’t be taken for granted. If you stop putting forth the effort, that success can depart just as easily as it came.

We’re about to complete the month of January, which is “1099 season”. It’s a very stressful period and, once we get through it, we’ll do something special to recognize the team.

But, we’re also already discussing what we can do to improve the process next year. Which brings me to my next lesson.

Never stop improving, but don’t change for the sake of change.

office people with hands togetherOver time, we’ve identified better ways to do things within the company. However, we have found that there are times when you have to accept that perfection is unattainable.

One area we have found this is particularly true is in the realm of project management automation. We’ve been able to put certain templates and systems into place to help cut down on both administrative and client hours. However, we found that we could only take that automation so far if we wanted to continue to offer highly-customized service. There might be a better solution out there that we have not found yet, but we can only dedicate so many hours to researching a better option (unless we want to limit the number of new clients we accept). Which leads me to my final point…

Everyone matters.

puzzle piecesIt’s always exciting to land a “big” new client, but some of my most-cherished client relationships are with those small, one or two-person companies. We have many clients who just come to us for a bit of training or help with their start-ups, and I’m the go-to person in the office to work with those, because I enjoy them so much.

Ironically, though this was never the intention, some of those small clients have led to big business. For example, I helped a local interior designer with cleaning up and training on her QuickBooks account. She connected me with a friend of hers in Charlotte, for whom I did some remote training. Those relationships led to referrals to other interior designers, until, suddenly, we found ourselves working with half a dozen new interior designer clients, a few of whom are very large and for whom we’re providing extensive services. And this all stemmed from helping someone who many other companies would not have given time to. (This makes me think of our first ever blog post, Nice Guys Finish First.)

Our little company is not so little anymore (and certainly not as little as when that first post was written). But we’re still learning, and still have so much to learn. I’m excited about what new lessons 2019 will bring.

financial report

"Your Business is Only as Good as Your Accounting System" by Dave Baldwin

This article may be a rude awakening for a number of small businesses. You may bake the best cupcakes, deliver the best massages, or engineer the fastest and most secure computer systems, and still be held back by your accounting system. It's a sad thing when businesses make amazing products or invest years of sweat equity to build a stellar reputation -- only to watch it all crumble because they didn't build a robust financial infrastructure to support it. The cold hard truth is that every business's accounting system (or lack thereof) is ultimately what makes or breaks the business.

What does accounting have to do with your competitive advantage?

charting financialsThe competitive advantage of a business is that which your competitor cannot easily duplicate. In Rule #1, investor Phil Town details the approach by which he follows Warren Buffet's methods for investing in companies. One of the criteria is what he calls "moats," or layers of protection around the proverbial castle that comprises a business. One type of moat is a well-established brand name. Even if a competitor builds a superior product at a lower price, they cannot copy or take away brand recognition. A strong brand does not guarantee success in itself, but it is a key factor in the longevity of a business.

Now, let's take a look at how management systems play a role in competitive advantage. Let's use a hypothetical example of two marketing agencies. Both agencies have highly creative talent. Both are well-known in their markets. Both work with high-profile clients. Both have a well-established track record for delivering great service. But they diverge in one area: accounting. We'll call them Agency A and Agency B.

Agency A has a basic nuts-and-bolts accounting system. They keep track of their costs, they know how much money they have. They know their cash flow, and they know their break-even point. They know how many client engagements they need per month to cover their overhead expense and taxes. The goal of Agency A's accounting system is to keep the lights on. And it works.

Agency B, on the other hand, looks at accounting differently. They aren't just trying to survive; their goal is to grow. Their goal is to dominate their space and scale their business to twice its current size over the next two years. They have built a system to support their objectives.

Now, let's take a look at the difference between their accounting systems.

Sales, Marketing and Revenue Forecasting

budgeting revenueAgency A knows how much revenue they bring in each month. They have a rough estimate of how much they are likely to make for the next six months, based on their recurring monthly revenue from regular clients as well as a few deals in the works that they expect will close soon. They exhibit at a couple of expos each year, and they've found that these usually generate enough business to pay for themselves. They don't feel the need to examine any data, because they know that certain marketing tactics work if you just do them. They don't take clients whose budgets are too small. They will never say no to a client with a big budget, unless they just can't do the work.

Agency B knows how much revenue they bring in from each of their major service lines, and they've used their accounting system to determine which types of services are the most consistently profitable. They track their marketing campaigns and sales activity relentlessly, and they pay close attention to how much it costs them to acquire each new customer. They notice where their best customers come from, and how many marketing touches each one required. Based on this data, they constantly fine-tune their campaigns and focus their advertising spending on the most effective marketing channels. They are sometimes surprised at what the data reveal. They are not concerned with how big or how small a client is; only whether the job is profitable and whether the client is a good fit. They take pride in their track record of starting with small clients and helping them grow. They have also walked away from multimillion-dollar accounts when the risk was too high.

Talent Utilization and Capacity

colleaguesAgency A tracks time spent on client projects with a reasonable degree of accuracy. They have a pretty good sense of how busy everyone is. They are very cautious about hiring, because they've made the mistake in the past of hiring too many people and then needing to let some go when business slowed down. They often use independent contractors and freelancers as a stop-gap measure when large projects come in or when work becomes unusually busy. They like having a flexible work force that can be called on an as-needed basis. Hiring full-time staff is generally a rarity unless someone leaves the company, so they usually do not advertise for new talent. When they do hire, they are often in a hurry to fill the position quickly because it is in reaction to a sudden upswing in work, so they can't be as selective as they would like to be.

Agency B is rigorous about utilizing their team's time and talent in the most effective possible way. They have broken down each service line into standard operating procedures, and they have defined benchmarks detailing reasonable time spans for completing tasks. When they notice that tasks are taking longer than usual to accomplish, they investigate to figure out why. Agency B's management carefully watches the team's capacity and is always advertising and interviewing candidates for their next team member. They are always anticipating growth, and they know when to pull the trigger on a new hire based on their sales pipeline and capacity of their current team. They view the next hire as inevitable, and they recognize that finding the right person may take time, so they are always advertising and interviewing whether or not they have an immediate need.

Company Culture

company cultureAgency A has a ping pong table and free coffee in their employee lounge. They take pride in having a hard-working team, but also a laid-back office. Employees generally like working there, and the pay and benefits are comparable to the rest of the industry. Communication is good overall, and people have a lot of flexibility to do their jobs in the way that they prefer- as long as the work gets done and the clients are happy. People sometimes work from home, and they enjoy the flexibility to adapt their schedules to the needs of their families, to a reasonable degree. There is no obvious path for advancement at Agency A, but management points out that there's plenty of room to grow for people who take initiative. They've been frustrated a couple of times when their best people left to take jobs in larger firms or to start their own businesses. There have sometimes been grumblings about inconsistencies in pay, but the owners feel that this is not justified.

Agency B has a no-frills workplace. Everyone discussed the idea of adding perks like a nicer employee cafeteria, but since the company has a generous profit-sharing plan, and everyone feels a sense of ownership in the company, no one wanted to spend the money on extraneous benefits. At Agency B, everyone loves their work. They know their numbers, and everyone is fantastic at what they do. There is never a boring day at Agency B, because they are always taking on new challenges. Since the company is always growing, new opportunities for career growth are always emerging. It is rare that the company makes a bad hire, and when they do, it becomes apparent quickly. The wrong people weed themselves out. There is a sense of friendly competition among the team. People work different schedules, but everyone is dedicated and working hard, and no one doubts it. Because everyone's job is measured against benchmarks, there is never any question as to who is performing and who isn't.

Which agency would you rather work for? Which one would you be more likely to invest in? Which one's services would you be more likely to retain?

Every single competitive advantage listed here, and countless others, all boil down to accounting systems. There is one difference between best-in-class businesses and average businesses, and it all boils down to their accounting systems. As boring as it might sound to some, the accounting system of a business is what creates the clarity and insight to make decisions. Businesses that have imprecise accounting systems tend to make decisions based on feelings, and people tend to perceive feelings as more accurate than they really are.

If you're weighing your options for next year and considering what investment of time and energy will make the biggest difference, the first place to look is your accounting system.

Dave Baldwin is an integral part of The Bookkeeper staff experienced in marketing and management consulting. His own entrepreneurial journey was spurred on by a desire to help introverted entrepreneurs succeed in business.


Planning to rent out a home? Be prepared.

Everyone likes a little extra income, and the "sharing" economy has made that easier than ever. For those with a second property, options like Airbnb and VRBO have become very popular as means of procuring rental revenues. However, renting a home through one of these services can include tax implications of which many are unaware. If you are operating as a landlord for short-term rentals, here are some things you should know.

What qualifies as rental property?

lodge rentalThe IRS has a great deal of information on classifying rental properties in Topic Number 415.

To be considered a rental property, the home in question cannot qualify as a residence. A residence is one in which personal use equals the greater of either 14 days or "10% of the total days you rent it to others at a fair rental price". So what does "personal use" mean, in this case? Personal use can be one of four scenarios.

1. When you or another individual who has an interest in the property (i.e., a business partner or co-owner) uses the property (unless that individual pays you a fair market price for rental). So, if your business partner's family uses the property for a vacation, that's personal use.

2. When a family member uses it without paying a fair price. If you let your niece rent it at half the usual rate while she's in town for the weekend, that's personal use.

3. "Anyone under an agreement that lets you use some other dwelling unit" Consider the rom-com "The Holiday", where Kate Winslet and Cameron Diaz swap houses with each other for a vacation. If you were to do something similar, those days spent at your house would county as personal use, since you were trading them for your own lodgings during that time.

4. Anyone at less than a fair rental price. This is self-explanatory, but also somewhat nebulous. Your best option is to have documentation supporting your pricing strategy, and apply it consistently.

Likewise, any expenses deducted must be deducted proportionally to the amount of time the home served as a rental. (So, if 5% of the year was personal use, only 95% of the appropriate expenses may be deducted.) If the property, in fact, does not meet the criteria to be considered a rental, you cannot deduct expenses on it. However, you also do not have to report rental income, in that case.

What can be deducted?

hardware toolsExpenses that are necessary for "managing, conserving and maintaining your rental property" can be deducted. These could include plumbing repairs, or cleaning services. You can also deduct expenses related to the business of renting out the property, such as any host fees from Airbnb, or advertising and legal fees related to the property.

You can also deduct any expenses which the tenant paid and which you then had to reimburse the tenant for. (For example, if the air conditioner breaks on the weekend, the tenant pays to fix it quickly, and you then reimburse the tenant, you can deduct that repair expense.)

You cannot deduct costs of improvements, those costs incurred in the act of restoring the property, or adapting it for a different use. You can, however, recover some of those costs on Form 4562 where you would report depreciation expenses.

Occupancy Tax

hotel2Many states and municipalities require landlords to collect and remit occupancy tax on short-term rentals. (It's a bit like a sales tax, but for hotels.) You will need to closely examine your local laws, as they can vary greatly on tax rates, what constitutes short-term rental, how frequently it must be remitted, etc. To further complicate the matter, occupancy tax may be collected by states, counties, AND cities.

Additional Taxes

moneyIf you were to sell your property, after it has been designated as a rental, you will need to report the income from the sale as capital gains, and pay capital gains tax on that accordingly. If you are a high-income earner, you may also be responsible for net investment income tax. (See IRS Topic Number 559.)


signing documentAs always, be sure that you are collecting W-9s from service vendors and following all applicable requirements for filing 1099s at year-end.

We work with a number of property owners, on these very issues every day.



When you're not a "startup" anymore...

All of "Hamilton" is great, of course, but, among the multitude of great lines, there's one in particular that always speaks to me as a business owner. During Cabinet Battle #1 (a rapped debate about America's fiscal strategy), Hamilton states to Jefferson, "Thomas, that was a real nice declaration. Welcome to the present; we're running a real nation."

Though the line is directly referring to conflict between the Federalists and Anti-Federalists, it always makes me think of the challenges startups face after they've achieved their first measure of success. You start with your own personal "Declaration of Independence" (from your previous job), start a company, and then just fight to survive. One day you wake up and it's a real business. The question then is, "Now what?"

Speaking from our own experience growing a fast-moving startup over the past five years, I wanted to offer our advice on what to do next when your startup grows up.


Scaling economically.

scaling economicallyIronically, in a lot of ways, it's easy for a startup to be profitable. The staff is small and working like crazy, and no one expects a huge salary or a ton of perks, so you get a lot of bang for your buck out of the few people you have. You probably don't have an office yet (maybe just a co-working space), so there's not that huge monthly expense hanging over your head. The overhead in general is low, and you're really putting your A-game out there for every possible sale.

Sure, it's not sustainable in the long-term (unless you are cool with regular nervous breakdowns), but in those early days you can often at least break-even, even if you're not rolling in the dough.

Eventually, you realize that your staff does need to grow, or that you do need a place everyone can work centrally. (Though you have to be careful not to add those costs just because they're things you want. See our prior article, Living a Lie: The mistakes that make entrepreneurs go broke.)

Scaling is not without its risks, but there are steps you can take to mitigate those risks. Having a budget is key, obviously, but it is also helpful to map out conditional budgets for if you add various expenses, such as rent (or if you were to have a slow sales month). You can use those to establish a set point for when you're willing to add to your overhead. (For example, once we are regularly at x recurring revenue, we will sign a lease on an office, or hire support staff.) This can allow you to scale at a safe pace, without over-expansion.


Managing changing stresses.

growing business stressWhen a startup is new, your main stressor is where the next sale is coming from. As the business grows and acquires clients in greater numbers, some of those stressors go away, and new stressors are added.

One of the biggest headaches in a growing company stems from managing a growing staff. When the company is small, you're operating in your area of expertise. As the company grows, you have to learn more about being a leader. Hiring and managing employees can take a mental toll, especially as you realize that the systems that worked when the company was smaller are no longer sufficient. (For instance, you will likely need to invest in a CRM that can help your new staff navigate their workload. Even if the original startup members don't need it, new employees will.)

Additionally, as you get more and larger clients, the clients themselves will require additional management. It can be hard to deliver the same level of personal attention when your time is spread so thin between them. It will become necessary to delegate some of the customer service duties to other staff (terrifying as that may be).

This is not to say you drop contact with clients, or aren't available when they need something; it just means you unload some of those duties onto other people, so the client can get what they need (even if they're no longer getting it directly from you).


Becoming who you are supposed to be.

writing your storyIt's not uncommon to feel a bit "lost" as your company grows. I experienced a small existential crisis the first time we signed and began work with a new client with whom I myself had never directly communicated. Once I got over the brief panic that I might no longer be needed, I realized how freeing it was, that I knew we could bring in revenue without my involvement. As we grew and hired additional staff, I didn't have to work on every single account; a new admin meant that I didn't have to manage the filing and calendar anymore.

I began to have something almost resembling "free time", and for me, that was terrifying. I had to figure out what to do with myself.

Fortunately, I really enjoy the study of business, in general. I began focusing on how we could improve processes, expand into new markets, and stay ahead of changing trends. I worked for us to become one of the first Xero-certified partners in our area, and began focusing on new business types (B-Corps, for example), so we could be prepared to serve upcoming businesses.

I also started focusing on who I wanted to be as a business leader, and who we wanted to be as a company. In a lot of ways, the company's growth has freed us to circle back to those original goals and mission statement. It's not enough just to grow a successful business; we want to stay in line with why the company was founded in the first place.

It's easy to imagine what you think a business owner should look like (see our article What makes an owner? for some prime examples) and fall into the trap of backing too far off from the company, or becoming an absentee owner. This is not what embracing your changing role means. It means that, instead of ordering business cards, you're calling referral partners (not that you're relaxing on a yacht while the minions do all the work).


It seems ironic that success should bring so many difficulties, but adapting to those new challenges is what sets companies apart. Be flexible, stay committed, and plan for everything you can, and you'll keep the fire you started growing strong.

Guest Post: Neal Isaacs, "Advice on Accountants (for what it's worth)"

VR Business BrokersToday's guest post is from Neal Isaacs. Neal Isaacs, MBA, CBI is a Business Broker and the owner of VR Business Brokers of the Triangle, located in Raleigh, NC. He writes about business and helps business owners discover their exit options. Call (919) 628-0571 or email [email protected] for your free consultation. Learn more at




As a business broker, I answer a lot of questions about how to sell a business.  One of my FAQs that I share with all business owners planning to sell is about the total cost to sell a business.  

People don’t think about costs in selling a business.  The first question people always think is “How much can I get?” but the truth is:


It’s not how much you make, but how much you keep that matters.


So how much will you keep?  What will be left depends on how much it costs to sell a business, as well as your tax treatment on what you get.  Costs toTall Buildings sell a business, if you don’t consider paying off your debts, are primarily professional fees. Consider the investment in a business broker, as most business sellers are doing it for the first time, and the sale of a business is a complicated and convoluted transaction, and consider the costs of a business attorney.


You’ll also want to consider the costs of a accountant.  Chances are sellers are already using these advisors, but there may be some additional costs for updating or adjusting P&L statements.  

Depending on your time frame for the sale of your business, there may be more that can be done from an accounting perspective to increase the value of your business from a buyer’s perspective.  Let’s consider:


How Far?

The “look-back” period for the sale of a business is normally three years, but some buyers will ask for five.  If you’re planning to sell your business in the next couple of years, it’s wise to communicate this fact to your accountant, and to start working with a business broker.  Preparing and highlighting the best financial aspects of your business is something a good business broker can help you with in conjunction with your accountant.


The fact of the matter is, running a business to sell is different than running a business to support a lifestyle.  The IRS has a lot of rules that your accountant will know and guide you on regarding how much you’ll have to pay in taxes, but a good accountant will also know how to protect you from paying too much tax in a legal and ethical manner.


How Much?

Cash money
It may sound obvious, but don’t be afraid to ask an accountant how much they charge, or at least to give you a range of what to expect.  Different accountants charge different prices for similar work because they have different costs to run their businesses, and they bring different experience to each opportunity, so interview your prospective accountant to learn if they are bringing the right skill and experiential sets that you need.  


Do We Fit?


When picking an accountant, it’s good to ask them about what their client base looks like.  You’re accountant will know exactly how much money you have, and the size of your business eventually, so consider being up front with them in your first meeting if for no other reason than to ask them if your business resembles their current book of business.  If your business is an outlier, they may simply not be reviewing the tax code and regulations related to the needs of your business.


Too Much?


I have seen one person pay $400/hour for financial due diligence on a deal for buyer representation, and it was way too much.  The CPA on the buyer’s side was more than willing to ask questions and go down paths that were not germane to the deal at hand, in part because he was being paid by the hour, and in part because his client hired him to investigate, and he was used to investigating very complicated businesses.  This was not a complicated business, and in my opinion this buyer brought a cannon to a knife fight (and paid for it).


Whether you’re a buyer or a seller, picking the right accountant, or even upgrading to the right accountant, can pay for itself.  Especially after the sale, when you have to deal with the financial repercussions of capital gains (this is another great question to ask your accountant early if you’re a seller).

If you need help choosing or interviewing an accountant in preparing for the sale of your business, I can help.  Email me at [email protected] and I’m happy to share some questions that you could ask an accountant that you’re considering hiring.