Tuesday, June 13, 2017

The Failed Sand Castle of Divvy

 “I’ve missed more than 9000 shots in my career. I’ve lost almost 300 games. Twenty-six times I’ve been trusted to take the game winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.” - Michael Jordan

I recently read Failing Forward, by John Maxwell.  There is an excerpt from the book which discusses how failure can be a valuable learning experience if we actually seek to understand it.

Maxwell uses an analogy from a Peanuts cartoon to illustrate the concept.  He cites an example of Charlie Brown building a sand castle on the beach which gets flattened by a wave.  Charlie Brown stares at his would be creation, knowing a lesson is in there somewhere but he doesn't try to figure out what it is.

Often times when people fail at something it sends them to a dark place or they have such a fear of failing that it paralyzes their effort to try.  As Maxwell explains, we must embrace failure for what it is, an opportunity to learn.  But we must put in the effort to learn from it.  This is what helps us grow and prevents us from making the same mistakes.  In Charlie Brown's case, he could have learned to build sand castles a little farther from the waves.

Taking the leap to become an entrepreneur is a big risk.  Waves are constantly washing up onto the shore and wiping out sand castles.  You know going in that the statistics are against you.  Most business fail.

A couple of years ago, I made the leap.  I set out to build my own sand castle.  And here I am about to pad that statistic even more.  I built my sand castle too close to the waves.  It is hard for me to call Divvy a failure though.

Don't get me wrong, this was a gut wrenching decision (if you haven't figured it out yet, I'm closing the business).  I started to go to that dark place.  I peaked in the door.  It wasn't pretty.  It was scary.  Holy sh*t it was scary!  And painfully negative.  I've been knocked down a lot.  I always have and always will get back up.  This time it seemed a bit harder to get up.

As I started to fall, I picked up my head and looked around me.  I got brutally honest with myself and my family (extended family and friends).  I asked for help.  I quickly realized there was a long line of people offering to help me get back on my feet.  I knew that the impact would be felt, but with help I could brace for impact then bounce back up.  It was time to embrace the suck (Marine speak... Shtuff just got real.  Deal with it.  Learn from it.  Move on.)

It is hard for me to call Divvy a failure.  I have learned more in the past 2+ years running this business than I had in the previous 10.  I learned a lot about life.  I learned a lot about myself.  I learned a lot about the people I associate with (and those I choose not to).  I learned a ton about business.  I met some of the most amazing people on the planet.  Seriously.  I met some people who were in the trenches too, hooking and jabbing out there in the entrepreneurial world, who I truly believe are going to change the world.  I got so far out of my comfort zone that I don't even remember where it was.  I put myself, and my tiny little company, in a position to pitch to execs at a Fortune 200 company.  I hustled, stumbled, tripped, and fell backwards into some great situations.  I built something from scratch (with a lot of help) that people paid their hard earned money for.  My clients are awesome!  There were even some people that wanted to join the team (they were crazy enough to want to get in the fight with me).  It has been an amazing experience, filled with daily roller coaster rides, lots of fun (and some heartburn), and a lifetime worth of lessons.

I did it.  I took the leap.  For those of you who know me well you know that Sinatra's song "My Way" should be playing in the background as you read this.  https://www.youtube.com/watch?v=6E2hYDIFDIU

At the end of the day, the business did not work out how I planned, or how I wanted it to.  If I looked at the sand castle that has been washed away and didn't learn anything from it, it would be a failure.  But I don't.  The sun will come up tomorrow, I'll wake up, and that will be a pretty good way to start my day.  I'll have an opportunity to take the lessons learned and apply them to my next adventure, whatever that may be.

To everyone who helped make this wild ride happen, THANK YOU!

“Learn from yesterday.  Live for today.  Look to tomorrow.” - Snoopy

Monday, May 22, 2017

Top 5 Processes Successful Financial Advisors Have In Place

We are all busy.  Life is busy.  Running a business is busy.  The word busy is even in the word business...sort of.  I make a motion to change the spelling of the word business to busyness.  All in favor say "I".... (crickets).  Moving on.

I get it.  Being a financial advisor is tough.  It takes a lot of hard work and dedication to succeed.  And don't even get me started on all the back office stuff you have to keep up with.

If you want to grow your practice you're going to have to find a way to spend as much time as possible in front of the right people building relationships.  Notice I didn't say telling them about the next hot stock.  Can I be frank (sure can I still be Garth...)?

You're not the best stock picker in the world.  If you were you'd be running a $10B hedge fund from your 100 ft yacht in the Caribbean.  Your value, as a financial advisor, to your clients is in the relationship.

What if you found the time in your busyness (still no?) to add one more meeting with the right person per month?  Per week?  Per day?  I'm guessing that would have a significant impact on your business.  So why don't you do it?  Why don't you build more relationships with the right people?

(insert laundry list of excuses)
At the end of the day it comes down to time.  You're too busy, right?  Life is busy.  The most successful financial advisors I know are very efficient with their time.  They have a process for everything so that their business is streamlined and they spend most of their time building relationships.  And remember your value, as a financial advisor, to your clients is in the relationship.  

After numerous conversations with some of the top advisors around the country, I came up with the top 5 processes successful financial advisors should have in place.

Marketing is the process of letting people know you understand a problem they may have, informing them about your solution to it, and giving them the chance to contact you for more information.  Lead generation.  Attracting potential customers to you.  The key to effective marketing is understanding your audience.  The ultimate goal is to position yourself as THE subject matter expert in a particular niche.  This can often be achieved by consistent messaging in relevant content via articles, advertisements and/or social media.  Too many advisors are generalists, which is why their marketing doesn’t work.

Prospecting, on the other hand, is you proactively reaching out to meet people who you may be able to help.  Similar rules apply to prospecting.  Too many advisors are generalists.  How many times have you met an another advisor at a networking event that works with HNW individuals that are 55+?  (yawn…just. like. everyone. else.).  Sure you do, boss.  My guess is you’re at that general networking event because you’ll work with anyone who is willing to give you their money.  And your pitch proves it.  That is why it isn’t working.  Think about the doctor analogy for a minute.  If you’re about to have open heart surgery, who do you want to do it?  Obviously you’d pick the heart surgeon over the family practitioner.  Your clients think the same way.  If you position yourself as THE subject matter expert for a particular niche, you can prospect in the places where your best clients will be.  Your elevator pitch should be consistent with the marketing messages you put out too.

First of all, it should go without saying but I see it constantly.  Be respectful of people’s time.  If you scheduled an hour, don’t let it take two hours.  If it gets close to the time acknowledge it and take the appropriate next step.  Have an agenda.  Stick to it.  Check for understanding of the agenda with your prospect/client. Keep some buffer time in it to allow for conversation, questions, and if they would like to add something.  There are several types of meetings you may have in your practice (intro, getting to know you, solution presentation, periodic review…).  Have a clear plan for each type of meeting.  It will simplify things for you and your clients will appreciate it too.

Essentially onboarding is another meeting (or series of meetings), but it is so important it is worth its own category.  The most important things to get right during the onboarding process are making the client feel welcomed/special and setting expectations.  If you get those things right life will be much simpler in your practice.  If not, well, brace for impact.  This is where you get to shine regarding how easy it is to do business with you. 

Financial Planning and Investing
How many advisors do you know that focus all of their time on generating returns across 100 different portfolios?  My guess is that none of them are top producers.  Top producers realize their value, as a financial advisor, to clients is in the relationship.  They are not trying to be the best stock picker in the world, because they are aware they are not.  They are aware that most people don’t need a complex solution.  They take a simple approach to investment management, focusing their time on client goals and planning.  As for planning, they also streamline that as much as possible.  They cover similar topics which each client and dive down the appropriate rabbit hole as needed based on how questions are answered.  They have a few key partners they work with that are on board with the process, bringing them in when their expertise is required.  

We are all busy.  Life is busy.  Running a business is busy.  Being a financial advisor is tough.  It takes a lot of hard work and dedication to succeed.  If you want to grow your practice you're going to have to spend your time wisely.   Your value, as a financial advisor, to your clients is in the relationship.  Spend your time deepening relationships and adding value.

Monday, April 3, 2017

Happy Birthday, Divvy!

It has been 2 years since I walked away from the corporate world and started Divvy Investments.  Running a business is a delicate balance between excitement and terror.  I am truly grateful for everyone who has helped get us this far.
A lot has changed in the past 2 years.  We started out working with diy individuals (still work with a few) but quickly realized we were a better fit for advisors.  We have fine tuned our quasi robo advisor.  We have fine tuned our niche.  Now we even do a little bit of marketing consulting on the side to compliment the models.  Our focus is helping independent financial advisors spend more time building relationships with the right people and less time in front of their computers.  We have had opportunities to do a handful of other things but for us it just made sense to put a laser focus on the little box and take really good care of our customers.  A lot has changed and I have a few more grey hairs.  
Our values have remained the same:
  1. Be passionate:  about life, family, friends, and our awesome customers
  2. Evolve via education:  learn something new and teach someone else
  3. Make Mama proud:  do the right thing
Those are here to stay.  Cheers!

Tuesday, March 28, 2017

3 Reasons Why Your Startup Should Hire Kindergartners

Chance (my son):  “Dadda, we should add another letter in the alphabet.”

Me:  “Really?  Why?”

Chance:  “My Letterland character doesn’t sound right.  C is supposed to sound like Clever Cat.  We need a letter that makes the CH sound.  (pauses briefly) Can I have a snack?”  (casually walks away as if he didn’t just turn my entire world upside down)

Me:  (Mind blown.  Jaw drops to the floor.  #geniuschild!)
**note- www.letterland.com is an awesome resource to help kids learn how to read.**

I have been on this planet for almost 40 years.  I have had the opportunity to lead and follow some of the greatest minds in the country.  I have a graduate degree from a top tier university.  I try to surround myself with innovative thinkers in the startup community.  Not once have I heard a comment so obvious yet so outside of the box.  Not.  Once.

I was excited.  Motivated.  I immediately wanted to hire my son (who is in kindergarten) to review my business plan.  I had so many questions.  There had to be some things right in front of my face that I was missing.  LIGHT BULB!  Maybe I could do a focus group with the kids in the neighborhood?  And it would be cheap too, all I’d need would be a box of popsicles and a homemade bike ramp!

Well, the popsicles melted while I was trying to build the ramp.  Apparently that shiny orb in the sky produces a lot of heat and as it turns out I’m not very handy.  Epic fail on the focus group I guess.  However, I did come across a couple of other resources that reinforced the idea of trying to think about business like a kid.

Chris Heivly, cofounder of MapQuest, wrote a book called “Build the Fort” (check it out here).  In the book he relates the experiences he had as a kid to building a startup.  Simple, yet effective ways to think about building and growing a business.

Carl Nordgren, entrepreneur and professor, wrote a book about a class he used to teach at Duke called “Becoming a Creative Genius (again)” (check it out here).   It discusses how we are born creative and helps us find ways to get back into that way of thinking.

From those books and numerous follow up attempts on the focus group, I’ve come up with the top 3 reasons why your startup should hire kindergartners.

1       Creativity
      Kids just go outside and play.  They make up games and rules as they go.  The games constantly evolve.  As more kids come out to play, they find a role for them.  They are creatures of creative action.  Imagine if your startup did that.  

2       No boundaries
      Kids know right and wrong, but they don’t allow their minds to have boundaries.  They don’t know how to give their minds boundaries.  They are little explorers.  What’s over here?  What is this?  How does it work?  It looks like it could be a good addition to my rocket ship.  Our minds are trained to only go so far down the rabbit hole.  It’s a stick.  I will put it in the yard waste bag.  Kid brains are designed to chase things all the way down the rabbit hole and then to dig another series of tunnels to come home.  Imagine the possibilities in your company if there weren’t boundaries.

3       Lack of fear/embarrassment
      When kids are playing they share their ideas and build upon each other.  When they think of something that sounds fun or adds value to the game, they blurt it out.  No fear.  They are just having fun and trying to continue to do so.  Adults often get self-conscious about voicing ideas and opinions.  Imagine if the people in your organization didn’t hold back.
Imagine what could happen to your business if you looked at it like a kindergartner.  You take creative action.  You don’t allow yourself boundaries in thought.  You encourage the sharing of ideas.  

Now, before I get emails from every labor lawyer in the country, lighten up.  I’m not actually encouraging people to hire (or condone hiring) kindergartners.  After all, it’s not practical.  They take naps during prime productivity time…

Thursday, March 2, 2017

Robot Love

"What is the robot version of Bro-mance?" - Homer Simpson via "The Simpsons"
"Ro-mance." - Homer's robot friend, Bender
What if humans could coexist with robots? Gasp! (the nerve)
Relax. I’m not talking about creating little half-human, half-robot babies here. I’m talking about not viewing robots as competition, but rather as a tool to use for enhanced service.
There have been countless articles pitting robo-advisors against human advisors. The robo world says they can do things better, faster, cheaper. The advisors say that the human element is the most important piece of a comprehensive plan. It’s like the old Miller Lite ad: “Tastes great! Less filling!” You both like the same beer! Stop fighting!
At the end of the day, robo-advisors and human advisors are both trying to do the same thing, help the individual better prepare financially. Imagine the possibilities if they created a Ro-mance, as Bender says. I know there are some firms that have adopted this idea but it is largely still a competition. The logic is that if the two team up and each focus on what they are good at, then everyone wins…especially the client. 

What Is a Robo-Advisor?

A robo-advisor is an automated, algorithm-driven investment tool that focuses on asset allocation and rebalancing using low-cost index funds. It is largely based on modern portfolio theory and efficient market hypothesis (academic theories that have been around a long time; opponents say “But now is way different…” Check your Google machine for more info).

Why Use a Robo-Advisor?

The goal of a robo-advisor is to minimize fees and remove emotion from investing. The whole world knows buy low and sell high. Emotion says buy when the market is going up and sell when you start to panic as it crashes. Emotion is usually not good when investing. 

What Is a Financial Advisor?

That is a bit more difficult to define. In broad terms they could potentially advise on insurance, investments and/or taxes. For our purposes we will focus on investments. There are brokers, who earn commissions on products sold based on suitability of your needs. There are planners, who charge a fee for planning and advice (often times as a fiduciary, which means they have to act in your best interest). They are regulated and licensed by FINRA, the SEC, and/or states.

Why Use a Financial Advisor?

Financial advisors provide a human touch which can lead to a better understanding of your goals and guidance to help you achieve them. They can help you come up with a comprehensive plan which may help you prioritize multiple goals, address insurance needs, assist with estate planning, and deal with complex financial situations.

The Ro-mance

Oftentimes a financial advisor spends a significant amount of time creating and monitoring portfolios for clients. How much value are they really adding there? Their real value is in the relationship. After all, if he or she was the world’s greatest stock picker wouldn’t they be running a $10 billion hedge fund? Advisors should get out from behind the computers and in front of more clients building relationships. 
How awesome would it be if you found an advisor who used a robo-advisor to complement their services? The human would look at where you are compared to where you want to be and help figure out how to make it happen. One small piece of that puzzle could be the robo-advisor for your investments. 
What that would mean for you is an advisor who understands you and your goals and provides a comprehensive plan, all while minimizing fees on your investments.
Love is in the air. Robos and humans can complement each other. It could lead to a budding Ro-mance. 

Tuesday, February 28, 2017

Asset Allocation 101 Part 2

On multiple occasions, I’ve mentioned the financial services industry’s incredible ability to confuse everyone – seriously, everyone. My goal is to help make a little bit of sense out of the mumbo jumbo in hopes that it helps people make better decisions. In previous series, we discussed basic investing and financial planning.
We recently started an asset allocation series to build up the foundation of your financial literacy house. In Part One of the series, we discussed what asset allocation is and why it’s important, and provided an overview of some common asset allocation strategies (one of which was not a get-rich-quick scheme). Today we will do a deeper dive into each of the four most common asset allocation strategies: strategic, dynamic, tactical, and core-satellite.
Strategic Asset Allocation
Strategic asset allocation (SAA) is a long-term approach that is designed to minimize the impact of emotions on portfolios. The goal is to create an appropriate mix of investments that balance risk and long-term returns.
The concept suggests that investors will benefit by staying invested in the markets and adhering to target allocations that reflect characteristics of the investor, rather than the performance of specific investments.
When the market is volatile, are you a Snoopy Joe Cool type, or are you more of a doom and gloom Charlie Brown type? Target allocation percentages for various asset classes (e.g. bonds, U.S. stocks, international stocks…) are selected based on the investor’s comfort level with risk, time horizon, and investment objectives. As those items change, the allocations may change, as well. The portfolio allocations are monitored periodically. Then, as the allocation percentages drift from the targets – as the markets go up and down – the allocations are rebalanced back to the risk aligned target percentages. It’s a more passive strategy that doesn’t change based on economic conditions.
Dynamic Asset Allocation
Dynamic asset allocation (DAA) is similar to strategic asset allocation in that both set target allocation percentages of asset classes. However, dynamic allocations may have several short-term adjustments to those allocations based on current and expected market and economic conditions. When using DAA, the focus is typically on the absolute return, not on comparing to an index/benchmark. Investors and managers who use dynamic asset allocation can achieve high returns if they are right regarding their assumptions on what the market will do. Obviously that is easier said than done, especially in flat and down markets. Pay attention to trading costs if you (or your advisor) use DAA, as it can get expensive.
Tactical Asset Allocation
Tactical asset allocation (TAA) is a more active approach. It involves constantly evaluating specific investments, looking for opportunities to take advantage of undervalued or overvalued assets. Those who use this strategy are typically looking for shorter-term gains from market inefficiencies where the market overreacted to something, though the investments could be held longer.
TAA proponents essentially act as appraisers, using fundamental and technical analysis of the investment, markets, and economic conditions to evaluate the value of an investment. If it appears to be undervalued, they buy it. If it appears to be overvalued, they sell it. Use caution here – if you’re investing outside of a retirement account, you should be aware of the tax implications of the shorter-term gains. Most people who use TAA have significant investing experience, as well as access to a lot of economic data.
Core-Satellite Asset Allocation
Core-satellite asset allocation involves launching a satellite into space that will manage your money while simultaneously strengthening your core…
Ok, not true, but it would be epic if it were! One part Elon Musk, one part Warren Buffet, one part Arnold (I won’t even attempt to spell his last name). Shaken, not stirred. Epic, I say – epic! But I digress… again.
Core-satellite asset allocation is a hybrid approach. There is a fundamental core to your portfolio, which serves as the foundation. The core portion will be more long-term strategic asset allocation (potentially dynamic asset allocation) tied to your individual risk tolerance. The satellite portion of the portfolio will consist of shorter-term, more tactical allocations. The more seasoned the investor, the more she may lean towards a larger satellite allocation. The more novice investor should probably lean towards a larger core allocation.
Hopefully now you have a basic understanding of asset allocation. There are a lot of different strategies out there, and picking the right one for you comes down to your personality, how involved you want to be, and a good advisor guiding you.
As originally posted at http://centsai.com/investing-experts/asset-allocation-101-part-2-common-strategies/

Monday, February 6, 2017

Marine to Veteran to Entrepreneur

Ok. I'm far from Captain America. But being a Marine, then a veteran, then an entrepreneur is sort of the dream, right?
I’ve always been drawn towards challenges. One day after high school I woke up and decided to look for the biggest challenge I could find. I quit my job and enlisted in the Marine Corps infantry. That night during our family dinner I broke the news like this… “Mom, I quit my job, joined the Marines, and leave in two weeks. Can you pass the salt?”
In hindsight I probably should have softened the blow a bit, but my parents came around after a brief nervous breakdown.
I entered USMC boot camp in the late ‘90s weighing 115 pounds. This resulted in more than my fair share of quarterdeck time. Fast forward six months (bootcamp + school of infantry) and what seemed like 10 million pushups later, I weighed 165 pounds. The Marine Corps pushed me harder, mentally and physically, during that first six months than I knew I could go. But I liked it. Sure there was a lot of BS but I understood the bigger picture. They were breaking me down to build me up stronger. They were forcing me to rely on others. They were forcing others to rely on me. They were teaching us to rely on each other to move towards common goals.
I served four years and got out as a Sgt of Marines, the best job in the entire Marine Corps. Throughout my time in the Corps I was taught many life lessons. I became comfortable with calculated risk. I was confident in my ability to move forward on an 80% solution knowing that I’d be able to adapt and overcome whatever was thrown at me. I learned about perseverance. I experienced huge highs and lows filled with excitement and terror, ultimately figuring out how to remain calm in situations of uncertainty. I was exposed to some of the finest leaders on the planet, who provided exceptional examples of how to lead from the front.
Most of all, I quickly realized that the Marine Corps (and life) is what you make of it.
As I transitioned out, I didn’t know what the next chapter looked like. I worked full time while attending college 1-2 classes at a time. Because of my military experience (and the recruiter being a Navy guy) I was able to get a sales manager gig at a Fortune 100 company. The work was OK but not very fulfilling. Like many vets, I wandered aimlessly for a bit, searching for that camaraderie I had with my old unit. There were pockets of it, but certainly not the same.
Shortly after I graduated from college the world began to fall apart financially. 2008. Being a Marine, I saw smoke and ran towards it. If there was ever a time people needed help with their money it was then. I got licensed and jumped into the financial services industry as a financial advisor. People were afraid. Paralyzed with fear. I felt as though I could be a voice of reason for them and help them. It was very rewarding.
Unfortunately the industry is set up largely to take care of people with lots of money. They have armies of advisors flocking to them constantly. The people who needed the most help though were the middle class, and they weren’t getting the same level of service as the rich people. During that time I became interested in low cost index funds, asset allocation, and something called Modern Portfolio Theory. It was my way to address the problem.
That is when the idea for Divvy Investments was born.
I wasn’t in a position to start a company at the time. I went to grad school, spent a few years in consulting, and ended up back in the corporate world again. In the corporate world I was frustrated a lot. At one point I was actually told to care less about customers. That was the moment I knew I needed to work for myself. I quit my job and started a business (after getting the blessing from my wife, of course).
I was excited. I was scared. I had an idea that I thought could be a viable business, but I didn’t have all the answers. It was a calculated risk. I was confident in my ability to adapt and overcome with an 80% solution from my training in the Marines. I knew I could remain calm while being faced with the uncertainties of running a business. I had learned years prior that life was what you make of it and I was passionate about helping people simplify investing.
I started Divvy Investments in April 2015 with the goal of helping DIY investors make better decisions with their retirement savings. Since then I’ve added a co-founder, gotten to pitch/speak at events around the country, and stumbled into another market, selling our robo advisor tool to other financial advisors. Helping people while doing what I love is very fulfilling. We have a long ways to go with our company to achieve our mission, but we are bringing in more money than we are spending which is a good start.
Being an entrepreneur is not easy. You never know what situation you’re going to encounter. There are highs and lows every day. Most businesses fail. It is tough. I think what gives us, as veterans, an edge is understanding the parallels between our time in service and entrepreneurship. We know the value of a clear mission. We know how to assemble/train teams with talented people. We understand how important it is to lead by example. We are driven by a sense of mission accomplishment. We’ve persevered, adapted, and overcome strenuous situations many times before.
I’ve always been drawn towards challenges. I’ve added a few more pounds since my days on active duty. Probably from the salt… That’s my story and I’m sticking to it.
Semper fi!
Nick Bradfield
As originally posted at http://the-military-guide.com/marine-veteran-entrepreneur/

Friday, February 3, 2017

7 Tips to Prepare for Tax Season

“In this world, nothing can be said to be certain except death and taxes.” – Benjamin Franklin
It’s that time of year again. No, no. I’m not referring to the time of year when people abandon their New Year’s resolutions, though that is probably true also. I’m not referring to the time of year when a new season of "Game of Thrones" is beginning…wait, is it? If so, stop reading this and commence binge-watching. I digress…
It is the time of year when accountants excitedly say goodbye to their families and begin crunching numbers into the wee hours of the morning. It is the time of year when some begin to get excited about what to do with their tax refunds while others repeatedly tell them that they are loaning money to the government. It is the time of year when receipts fill shoeboxes. It is the time of year when we realize we should have saved receipts (Doh!). 
It is…TAX SEASON (insert horror film scream).
Don’t worry. The only thing to fear is fear itself…and perhaps going to jail for tax evasion…but mostly just fear itself. Instead, focus on these tax tips to help you get through the season.

7 Tax Season Tips

  1. Don’t wait until the last minute. Get a head start. It is much more relaxing and gives you time to adjust to surprises if needed. Procrastinating could lead to mistakes. Mistakes could lead to fines. Fines could lead to jail.
  2. Get organized. As with most things in life, the more organized you are the smoother things tend to go. Hopefully, you took a little bit of time periodically throughout the year to organize things. If not, just do it. Take a day and chalk it up as a loss. Get it done. Get organized yesterday. It will help clear your head and make your CPA happy (and probably save you money as a result). Remember to include all sources of income. Income, expenses, receipts…categorize them all. 
  3. Deductions. Take advantage of all the deductions you are allowed.
  4. Stay organized. You took the time to get organized. Now keep it that way.
  5. If you own a business, make sure to send out W2s and 1099s to your team. Here is a link to the IRS site which will help you figure out how to handle contractors. If you don’t own a business, gather all of your income statements for all of your income sources.
  6. To DIY or not to DIY? That is the question. You know your business. CPAs know theirs. If your situation is easy and you understand what you’re doing, give it a whirl. There are several software tools out there to help you do it yourself. If you are hesitant at all, it is probably best to hire an accountant. Ask people you trust who they use. Find someone you like and trust. If you own a business it would help if the accountant understood your industry and your business.
  7. Double-check your work or have your accountant walk you through it before submitting. It takes a little bit of extra time, but a lot less time than having to file an amendment.
“This is a question too difficult for a mathematician. It should be asked of a philosopher" (when asked about completing his income tax form) – Albert Einstein
Full disclosure: I am not a CPAEA, or any other tax professional. In fact, I can barely spell tax. Asking me a tax question will prompt the response of a blank stare. I’m just an organized guy who likes to keep things simple. I’m also friends with a lot of CPAs and recovering CPAs. I’ve heard them complain and seen them stress out when people don’t do the things above. Raise a glass to a healthy and happy CPA and a less stressful tax season for all! (For more from this author, see: How to Deal With the Stress of a Small Business.