Clint Costa is an attorney and CPA with the Chicago law firm of Harrison & Held, LLP, working with startups, entrepreneurs, and privately held companies on all manner of official-sounding legal and tax matters. Reach Clint at [email protected] or (312) 803-7104.

 

Recent posts by this Author


Whether You Like it Or Not, You Should Know How Daily Deals are Taxed

You don’t have to be the next Groupon to include a daily (or less frequent) deal component into your business model.  Many startups now are incorporating group buying or instant discounts into their offerings.  When they do, important tax considerations come into play. Fair…

InfoActive is Making Content Marketing Easy

Infographics – they’re interesting, useful, and the most important thing to happen to content marketing since teenagers started making money off their Zelda blogs. InfoActive, the award-winning* startup of well-traveled, Chicago-based entrepreneur Trina Chiasson, makes it easier to create high-value, mobile-friendly, beautiful and interactive infographics….

Swift Expo Cofounder, Serial Entrepreneur is No Joke

Bob Gillespie treats startups as no laughing matter.  He’s an expert, too, as both a former stand-up comedian and a current serial entrepreneur with two successful exits already under his belt. Bob and his cofounder, Matt Dabney, intend to disrupt the world of trade…

Chicago Starters Learn Lessons, Look Good at Stock Manufacturing Co.

The realization that a startup just isn’t working is a tough one.  Startup blogs far and wide claim that sticking to it and persevering through adversity are key ingredients to success.  And while that is certainly true, sometimes it just isn’t working. That’s what…

Law School for Entrepreneurs: Indemnification Clauses

Reading contracts – it’s not as cool as growth hacking, and it’s not as sexy as raising a Series A round.  But it is necessary for every entrepreneur to have a basic understanding of common contract provisions, which can help save both time and money. …

2 Ways for Entrepreneurs to use the Awesome Power of VentureDocs

VentureDocs is one of many startups attempting to attack the ancient and staid profession of law.   Most of these startups are focused on the related questions of: “how do I find a lawyer/how do I find a client?”  VentureDocs, on the other hand, is…

FasPark: 3 Lessons from a Disruptive Parking Startup

FasPark is a Chicago-based startup whose mission is to solve the ever-vexing problem of finding street parking in crowded urban areas.  Available right now in Chicago and Munich (and soon to begin in six other U.S. and international cities), the FasPark technology is different…

4 Reasons Why Startups Should Go Old-School with Their Banker

Entrepreneurs are, by definition, a self-reliant bunch. It makes sense, of course. Those who forego a paycheck and traditional job security in furtherance of an unproven business model are unlikely to need much hand-holding. Enter the banking relationship. Of all the old-line professions going…

Student Loan Hero Wants to Help You Pay your Student Loans

An American, a Canadian, and a Russian go to Chile… Sounds like the beginning of a bad joke your uncle might tell at Thanksgiving. Instead, it could be the start of an awakening for the increasing number of Americans leaving college and graduate school…

Slicing Pie: Rapid Reaction by a Boring Lawyer

In a recent Tech Cocktail article, Mike Moyer writes about slicing pie. In other words, how entrepreneurs should focus on splitting up equity in an early-stage startup. Moyer summarizes his concept of the Grunt Fund, in which equity in a startup is allocated to…

Want to Sue? Read this First [Part 2]

In a prior post, I explained that before you, as a business owner, spend any time or money fighting or litigating, you need to determine if you are willing to actually file a lawsuit. If not, then your time and money are better invested…

Want to Sue? Read this First [Part 1]

Inevitably, your business will face a dispute. It might be a founders’ divorce or it might be a claim against a customer, but no matter what it is, you will have to weigh the decision to spend time and money to litigate. Business disputes…

4 Secrets of the Tax Magician: The 83(b) Election

Last month I discussed the 83(b) election for income tax purposes, and how it can be used to entertain and mystify your key employees. A proper 83(b) election has various requirements imposed by the IRS, and unlike proverbial horseshoes and hand grenades, close doesn’t…

4 Ways to Defuse the Due Diligence Time Bomb

A dark and insidious being is growing stronger and stronger in your office while you are out conducting business. Customer contracts, leases, organizational documents, employee reviews, invoices, notices from the government – all of this paper will coalesce at some point with the goal…

Entertaining Key Employees with Tax Magic: The 83(b) Election

So you want to give your employees equity in your growing business. But stock options seem so 1999 and phantom stock sounds like a lot of paperwork. What to do? Restricted stock. It’s a relatively straightforward concept in most cases and usually pretty easy…