Podcast Recommendation: The Distance

thedMany of the podcasts I listen to aren’t financially-related, but I’ve recently been catching up The Distance Podcast which profiles the owners of private businesses that have been around for at least 25 years. Here’s their own description:

What’s the hardest thing about business? Not going out of business. The Distance features stories of private businesses that have been operating for at least 25 years and the people who got them there. Hear business owners share their stories of hard work, survival and building something that lasts. The Distance is a production of Basecamp, the company behind the leading project management app.

A few observations after several episodes:

  • If you’ve been around for 25 years, then you are both (1) good at what you do and (2) you turned down buyout offers.
  • These businesses were not highly-leveraged with debt, and thus could survive the lean times like the 2008 financial crisis.
  • Many of these founders could have sold for a sizable sum and retired (at least modestly) years ago.
  • Why didn’t they sell? For one, they have pride in the their work. Building houses, growing food, carving ice sculptures, or making cardboard boxes. It matters to them that it is done “right”. They feel loyalty to their employees and community.
  • Some are workaholics. If you’re going to always work, why not be the boss? If you sold, you’d have to start over or work for someone else.
  • These businesses are often kept in the family. Keeping it around to pass down to the next generation is another reason not to sell.
  • Some might only be in it for more money. But that seemed to be rare.

Most mass media business profiles focus on multi-national corporations (Apple) or some hot-shot tech unicorn (Uber). I found myself having a soft spot for these mom-and-pop businesses that stubbornly do their own thing.

IRS Estimated Taxes Due Dates 2016

irsclipIf you have self-employment or other income outside of your W-2 paycheck this year, you may need to send the IRS some money before the usual tax-filing time. Here are the due dates for paying quarterly estimated taxes in 2016; they are supposed to be in four equal installments. This is for federal taxes only, state and local tax due dates may be different.

IRS Estimated Tax Payment Calendar for Individuals

Tax Year / Quarter Due Date
2016 First Quarter April 18, 2016 (Monday)
2016 Second Quarter June 15, 2016 (Wednesday)
2016 Third Quarter September 15, 2016 (Thursday)
2016 Fourth Quarter January 17, 2017* (Tuesday)

 
* You do not have to make the Q4 payment due January 17, 2017, if you file your 2016 tax return by January 31, 2017 and pay the entire balance due with your return.

Who needs to pay estimated taxes?
In general, you must pay estimated tax for 2016 if both of the following apply:

  1. You expect to owe at least $1,000 in tax for 2016, after subtracting your withholding and refundable credits.
  2. You expect your withholding and credits to be less than the smaller of
    • 90% of the tax to be shown on your 2016 tax return, or
    • 100% of the tax shown on your 2015 tax return. Your 2015 tax return must cover all 12 months.

If you forget to pay (like I’ve done before), then you should make a payment as soon as possible even though it is late. This will minimize any penalty assessed.

How do I pay? When does the payment count?

  • By check. Fill out the appropriate IRS Form 1040-ES voucher (last page of the PDF) and snail mail to the indicated address. The date of the U.S. postmark is considered the date of payment. No fees besides postage.
  • By online bank transfer. You can store your bank account information and pay via electronic funds transfer at EFTPS.gov or call 1-800-555-4477. It takes a little while to set up an online account initially, so you’ll need to plan ahead. For a quick one-time payment, you can also use IRS Direct Pay (just introduced in 2014) which does not require a sign-up but it also doesn’t store your bank account information for future payments. Both are free, there are no convenience fees. The date of payment will be noted online.
  • By debit or credit card. Here is page of IRS-approved payment processors. Pay by phone or online. Fees will apply, but the payment will count as paid as soon as you charge the card. You may also earn rewards on your credit card. Check if there is a discounted fee available via limited-time promotion.

How much should you pay in estimated taxes? You’ll need to come up with an expected gross income and then estimate your taxes, deductions, and credits for the year. The PDF of Form 1040-ES includes a paper worksheet to calculate how much in quarterly estimated taxes you should pay. You can also try online tax calculators like this one from H&R Block to estimate your 2016 tax liability, and divide by four quarters.

How To Generate and Issue Your Own 1099-MISC Forms

1099blanksDid you as a small business pay another person or unincorporated business more than $600 total in the last year for services rendered? You may have to provide them a 1099-MISC form.

Here are the specific rules as laid out in the official IRS Form 1099-MISC Instructions [pdf]:

The Internal Revenue Service (IRS) requires businesses (including not-for-profit organizations) to issue a Form 1099 to any individual or unincorporated business paid in excess of $600 per calendar year for services rendered. This is required whether these payments are spread out over the course of the year or are paid in one lump sum payment. The most effective way to obtain the information needed to prepare the Form 1099 is by requiring that an IRS Form W-9 be completed prior to any payment being made. The penalty for failure to file Form 1099 can be as much as 50% of the amount paid for services.

Note that last sentence: The penalty for failure to file Form 1099 can be as much as 50% of the amount paid for services.

The 1099-MISC forms must typically be sent out to independent contractors by January 31st following the end of the tax year in which you made the payments. (As 1/31/16 is a Sunday, the deadline is February 1st for 2016.) You must also file a Form 1096 and submit the information to the IRS by March 31st.

If you’ve got your own accountant or payroll service, then you can pay them to generate the proper forms and send out these 1099s. However, I have done it myself as well, it is not very difficult. Here are your options for generating and issuing a Form 1099:

  • You can order physical, blank 1099 forms from the IRS for free, but it may take up to 4-6 weeks. Here is the IRS.gov order page. You’ll need at a minimum, Form 1099-MISC and Form 1096. You then print it out yourself and mail it. Cost: Free.
  • You can buy physical, blank 1099 forms at an office supply store like Staples or OfficeMax. You then print it out yourself and mail it. Cost: ~$30 for a kit of 24.
  • You can order physical, blank 1099 forms online. Here is the top-reviewed blank 1099-MISC kit from Amazon.com which includes multiple copies, envelopes, and 1096 forms. You then print it out yourself and mail it. Cost: ~$22 shipped for a kit of 25.
  • You can use a 3rd-party online service where you fill out the information online and they’ll create a PDF for you. The most popular is Intuit’s version (they make TurboTax). You will still need to print it out and mail the 1099 forms to your independent contractors, but they will e-file the information to the IRS. Cost: ~$15 for up to 3 forms, $4 each additional.
  • You can use 3rd-party desktop software where you will be guided as with tax software as to how to fill out the appropriate forms. The most popular is TurboTax for Business (not the personal edition), which will provide guidance and generate both 1099-MISC and W-2 payroll forms for you. It comes with a 60-day money back guarantee from Intuit, so if it doesn’t work to your satisfaction, you can return it within 60 days for a full refund. Cost: ~$105 for tax filing software which includes unlimited 1099 and W-2 forms.

Note that cannot use the blank 1099 PDFs that you find online; they are only examples.

Finally, remember that your first job is to get a W-9 form [pdf] filled out by the person you paid, so that you’ll have their Tax ID to enter onto your tax forms.

IRS Estimated Taxes Due Dates 2015

irsclipIf you have self-employment or other income outside of your W-2 paycheck this year, you may need to send the IRS some money before the usual tax-filing time. Here are the due dates for paying quarterly estimated taxes in 2015; they are supposed to be in four equal installments. This is for federal taxes only, state and local tax due dates may be different.

(Note: January 15th, 2015 is the last day to make an estimated tax payment for 2014. See bottom of post for fast payment options. This will prevent any penalty for late payment of the last installment. You do not have to make this Q4 payment if you file your 2014 tax return (Form 1040) and pay the tax due by February 2nd, 2015. If you miss these dates, file your return and pay as soon as possible to minimize penalties.)

IRS Estimated Tax Payment Calendar for Individuals

Tax Year / Quarter Due Date
2015 First Quarter April 15, 2015 (Wednesday)
2015 Second Quarter June 15, 2015 (Monday)
2015 Third Quarter September 15, 2015 (Tuesday)
2015 Fourth Quarter January 15, 2016* (Friday)

 
* You do not have to make the Q4 payment due January 15, 2016, if you file your 2015 tax return by February 1st, 2016.

Who needs to pay estimated taxes?
In general, you must pay estimated tax for 2015 if both of the following apply:

  1. You expect to owe at least $1,000 in tax for 2015, after subtracting your withholding and refundable credits.
  2. You expect your withholding and credits to be less than the smaller of
    • 90% of the tax to be shown on your 2015 tax return, or
    • 100% of the tax shown on your 2014 tax return. Your 2014 tax return must cover all 12 months.

If you forget to pay (like I’ve done before), then you should make a payment as soon as possible even though it is late. This will minimize any penalty assessed.

How do I pay? When does the payment count?

  • By check. Fill out the appropriate 1040-ES voucher (last page of the PDF) and snail mail to the indicated address. The date of the U.S. postmark is considered the date of payment. No fees besides postage.
  • By online bank transfer. You can store your bank account information and pay via electronic funds transfer at EFTPS.gov or call 1-800-555-4477. It takes a little while to set up an online account initially, so you’ll need to plan ahead. For a quick one-time payment, you can also use IRS Direct Pay (just introduced in 2014) which does not require a sign-up but it also doesn’t store your bank account information for future payments. Both charge no convenience fees. The date of payment will be noted online.
  • By debit or credit card. Here is page of IRS-approved payment processors. Pay by phone or online. Fees will apply, but the payment will count as paid as soon as you charge the card.

I usually pay online at EFTPS.gov for both convenience and to avoid fees. However, right now the lowest fee for a credit card payment is 1.87% from providers like PayUSATax.com, which I’ve used. Meanwhile, you can earn up to 2% cash back from a credit card like the Citi Double Cash card. So you can actually clear a small profit by making your tax payment with the right credit card, and it will officially count as paid to the IRS immediately.

Sources: IRS Pub 505, IRS Pub 509, IRS Form 1040-ES [pdf].

IRS Estimated Taxes Due Date Calendar 2013

Reminder for last quarter of 2013. If you’ll earn income outside of your W-2 paycheck this year, you may need to send the IRS some money before the usual tax-filing time. Here are the due dates for paying quarterly estimated taxes in 2013; they are supposed to be in four equal installments. This is for federal taxes only, state and local tax due dates may be different.

Tax Year / Quarter Due Date
2013 First Quarter April 15, 2013 (Monday)
2013 Second Quarter June 17, 2013 (Monday)
2013 Third Quarter September 16, 2013 (Monday)
2013 Fourth Quarter January 15, 2014* (Wednesday)

* You do not have to make the Q4 payment due January 15, 2014, if you file your 2013 tax return by January 31, 2014.

Who needs to pay estimated taxes?
In general, you must pay estimated tax for 2013 if both of the following apply:

  1. You expect to owe at least $1,000 in tax for 2013, after subtracting your withholding and credits.
  2. You expect your withholding and credits to be less than the smaller of
    • 90% of the tax to be shown on your 2013 tax return, or
    • 100% of the tax shown on your 2012 tax return. Your 2012 tax return must cover all 12 months.

If you forget to pay (like I’ve done before), then you should make a payment as soon as possible even though it is late. This will minimize any penalty assessed. This is all taken from IRS Form 1040-ES [pdf].

How do I pay?

  • By check. Fill out the appropriate 1040-ES voucher (last page) and send to the indicated address. If it is postmarked by the due date, the date of the U.S. postmark is considered the date of payment.
  • By online bank transfer. You can link your bank account and pay via electronic funds transfer at EFTPS.gov or call 1-800-555-4477. No convenience fees. It takes a little while to set up an online account, so plan ahead.
  • By debit or credit card. Here is page of IRS-approved payment processors. Pay by phone or online. Fees will apply.

I usually pay online at EFTPS.gov for both convenience and to avoid fees. In rare cases with the right credit card promotion, it can be worth it to pay the credit card processing fee. For example, last year I paid taxes with my Chase Ink Bold card. I paid $189 in fees, but earned $500 of bonus points.

Self-Employed Lifestyle Design from the 1970s: The Incredible Secret Money Machine Book

What is success? Perhaps you think of a new idea, get some venture capital, grow and scale like crazy, and then you sell it after a few years for mega-millions. More traditionally, you work your way up the corporate ranks, become a manager/executive, and make good money that way. Or perhaps you start a small business and expand it over decades. All are good and fine.

However, there are people out there that take yet another path. Their priority is to be able to do what they enjoy without interference and get paid adequately for it. These micro-businesses are self-funded, independent, and happy that way despite the inherent drawbacks. One person. No bosses. No employees. Some get rich, some don’t.

Which bring me to this book, The Incredible Secret Money Machine by Don Lancaster (see free download link below). First published in 1978 and updated in 1992, this is one of the few books that I’ve found that celebrates the idea of a person working for themselves and that being enough. There is a lot of outdated references in the book along with a “hippie” vibe, but also a lot of timeless ideas. To give you an idea of whether your personality aligns with this book, here are his four basic beliefs:

1. You have to be heavily into a technical or craft trip on a total lifestyle basis.

The absolute single most important thing in your life has to be doing something technical or artistic in a better and a different way than anyone else. […] Your own trip has to be the absolute center of everything you do, everything you work with, and everything you believe in. Doing it has to be much more important to you than making money, more important than worrying about what people think, and more important than behaving, competing, or complying the way that other people think you should.

2. You must want to stay in control.

[Read more…]

Flowchart: Should You Work For Free?

Here’s a decision chart that’ll amuse those of you who work independently, perform some freelancing/consulting work, or just happen to be especially good at something. Should you do the work for free? Well, it depends:


(click to visit site)

By Jessica Hische at ShouldIWorkForFree.com.

eBay, Half.com, PayPal, Amazon.com Sellers: 2011 IRS 1099-K Regulations

I just received the following e-mail from Half.com, where I occasionally sell used books:

We’re writing to let you know that starting with transactions occurring on or after January 1, 2011, new Internal Revenue Service (IRS) regulations require Half.com (and other businesses that process payments) to file a Form 1099-K for all sellers with more than 200 transactions and $20,000 USD in sales per year.

If you’re a high-volume seller who has met or is close to meeting the IRS thresholds, we may need to generate a Form 1099-K for you. If you have multiple accounts, we’ll take all of them into consideration when calculating your volume status. If you exceed the IRS thresholds, we’ll send your first Form 1099-K to you in early 2012. Your Form 1099-K will give you a consolidated report of all payments received through Half.com for 2011. This information will also be reported to the IRS.

Apparently, as part of new legislation designed to help track down (and tax) unreported income, starting in 2011 any credit or debit card payment processor with clients that have more than 200 transactions and $20,000 in sales per year must file a 1099-K with the IRS.

In addition to Half.com, this also includes individual sellers using services like PayPal and Amazon.com. Perhaps also sites like Etsy and Zazzle? This won’t affect me, but I think it’s a pretty good idea. I do feel that lots of eBay income goes unreported, and the limits are reasonable. If you’re clearing 200 transactions and $20k in payments, you should be tracking your income and expenses like a business. This 1099-K won’t really matter as it just reports gross amounts.

I’m more scared about the upcoming changes in 2012 that says that a business has to file a 1099-MISC for any person or business it pays more than $600 in a calendar year. Corporations are no longer exempt. That’s a ton of 1099 forms swirling around. I’m going to have to send W-9 forms to everyone from Staples to my web hosting company. I still hope they’ll change this rule before it goes into effect and swamps tons of small businesses.

More info: CNN Money, Journal of Accountancy, Stop1099.org

Two Completely Different Ways to Boost Productivity

While procrastinating today, I of course ran across a couple of tips on productivity and success that both powerful and very different.

First is an essay called Good and Bad Procrastination by Paul Graham. It includes a lot of insights into procrastination, and my favorite was the idea that it was okay to put off less important, scheduled, to-do list-type things whenever you get a chance to focus and do some really great things:

The reason it pays to put off even those errands is that real work needs two things errands don’t: big chunks of time, and the right mood. If you get inspired by some project, it can be a net win to blow off everything you were supposed to do for the next few days to work on it. Yes, those errands may cost you more time when you finally get around to them. But if you get a lot done during those few days, you will be net more productive.

In fact, it may not be a difference in degree, but a difference in kind. There may be types of work that can only be done in long, uninterrupted stretches, when inspiration hits, rather than dutifully in scheduled little slices. Empirically it seems to be so. When I think of the people I know who’ve done great things, I don’t imagine them dutifully crossing items off to-do lists. I imagine them sneaking off to work on some new idea.

The second is the Jerry Seinfeld Productivity Secret by Brad Isaac:

He told me to get a big wall calendar that has a whole year on one page and hang it on a prominent wall. The next step was to get a big red magic marker.

He said for each day that I do my task of writing, I get to put a big red X over that day. “After a few days you’ll have a chain. Just keep at it and the chain will grow longer every day. You’ll like seeing that chain, especially when you get a few weeks under your belt. Your only job next is to not break the chain.”

“Don’t break the chain,” he said again for emphasis.

This idea of incremental change is not new – see this post on Kaizen for example.

Some things are best achieved when you attack it a little every day – things like debt reduction, learning a language, or weight loss. Other things you may have to wait for the inspiration, but when it comes, it pays to put it above all else. Perhaps a great business idea or investment opportunity.

Chart: Unemployment Lasting Way Too Long

Above is a chart of the median duration of unemployment from the past 50 years, based on data supplied by the US Department of Labor. That’s quite a scary spike we have going right now. (Chart source, via The Atlantic and Greg Mankiw.)

Not coincidentally, the Senate just voted to extend employment benefits again after much debate. This means that the federal government will continue to provide up to 99 weeks of unemployment assistance, including the first 26 weeks provided by individual states.

People will argue whether this is the best way to combat the problem. I don’t know the answer, especially with the huge deficit, but I do feel that with two years of unemployment available that there is less excuse not to learn some new marketable skills if you need it. Also, this just makes my cash hoard of a year’s worth of expenses that much more important to me. I really didn’t think an emergency fund would provoke such a strong psychological response, but it has significantly lowered my daily stress levels.

If you don’t have your warm fuzzy cash hoard yet, open a separate online savings account and start socking something away! Just look at the chart again if you need motivation.

Amazon Kindle Most Highlighted Passage

The most highlighted passage on the Amazon Kindle eBook device is:

…the more money they made the next day on the streets. Those three things—autonomy, complexity, and a connection between effort and reward—are, most people agree, the three qualities that work has to have if it is to be satisfying. It is not how much money we make that ultimately makes us happy between nine and five. It’s whether our work fulfills us.

From the book Outliers by Malcolm Gladwell. Full list via MR and @willwilkinson.

Healthcare Reform Highlights For The Self-Employed

Until now, I haven’t written much about healthcare reform issues – it’s just feels so daunting and politically-charged. I do support the eventual separation of work and health insurance, as I think that all unemployed, partially-employed, and self-employed individuals should get access to affordable healthcare. As the dust settles a bit, I took a look through the many attempts of media to break down the healthcare reform bill into manageable bites. Here are my notes:

2010

  • Employers with fewer than 25 employees (more if you have part-time employees) and less than $50,000 in average wages may be eligible for tax credits worth up for 35% of paid premiums. Note: The tax deduction is not available to sole proprietors, so you may want to consider an LLC or corporation form.
  • All health insurance plans must allow people to maintain dependent coverage for children until they turn 26. This could help out the many young and self-employed. Also prohibits insurers from denying coverage to children because of preexisting health problems.
  • If you are self-employed and have medical conditions that make it hard to find any health insurance at all, there will be a high risk pool set up to create “affordable” premiums. I wonder how affordable that will actually end up being.
  • Insurers will no longer be able to put lifetime limits on coverage, or cancel policies that are already in service (except for fraud).
  • Starting September 2010, all coverage must include basic preventive care. As many small businesses can now only afford catastrophic coverage, this may mean additional benefits.

2011

  • Companies with less than 100 employees will be eligible for grants to set up wellness programs. Employers can offer employees bonuses of up to 30% of the cost of insurance.

2013

  • Limits medical expense contributions to tax-sheltered flexible spending accounts (FSAs) to $2,500 a year, indexed for inflation. (I wonder how much it costs to administer one of these for a self-employed person.)

2014

  • All U.S. citizens and legal resident must have health insurance, or else pay a fine. People who are satisfied with their employer-provided coverage don’t have to do anything.
  • Health plans no longer limit coverage based on preexisting conditions, or charge higher rates to those in poor health. Premiums can vary only by age, place of residence, family size and tobacco use. Wow!
  • Individuals and small businesses with up to 100 employees will be able to shop for coverage from newly-created health insurance exchanges. Theoretically, this will allow individuals to get rates just as competitive as current large group plans.
  • Small business owners who purchase coverage through the exchanges can receive a two-year tax cut for up to 50% of what they contribute toward their employee health insurance premiums.
  • Individuals may receive income-based tax credits for insurance bought from the exchanges. Sliding scale credits will eventually phase out for households above four times the federal poverty level, until about $43,000 for an individual or about $88,000 for a family of four.

Sources: CS Monitor, Health Reform and Small Business, USA Today, HealthReform.gov