Taxes: Stop Making It so Hard for Independent Contractors to Pay

If you are an independent contractor then you understand the pain of taxes! The process of paying taxes is the bane of my existence. For the non-believers, I'll take you through why it is so onerous.

First, taxes have to be paid EVERY quarter. This rule incentivizes you to keep up with your taxes and make sure you make the payments on time. Fundamentally, this is good, but it's super annoying. You have to remember each quarter to submit your taxes or you get a penalty fee. This fee and the tax debt accrue interest. In conclusion, don't forget to pay your taxes or Uncle Sam will be collecting a ton of additional interest and fees.

In order to file your taxes, you have to submit a 1040ES. This means that you have to estimate your taxes every quarter. This is both annoying and worrisome. How do I know that I have estimated the correct amount? The answer to that question is YOU DON'T. You may end up owing additional taxes if your estimate is too low. I'm not sure if they add fees or interest if you pay below the required amount. If you overpay, the government keeps your hard earned money interest free. Both scenarios are annoying.

To avoid any tax issues, I signed up for Zen99. This was a Y-Combinator company that helped independent contractors handle all of their tax needs. A month after signing up for the service, the CEO announced that they were closing down the company.  As a side note, I got the chance to get on a call with the founder of Zen99. It was a very insightful conversation and it sounded like he had several good reason for shutting down the platform. Nonetheless, this action left me screwed.

The problem is growing as more and more people opt to be their own boss and freelance. I hope that I have paid enough taxes these last few quarters. But I don't know. I hope that another startup finds a way to help independent contractors with taxes. 

Efficiencies from Computers will Make the Rich even Richer.

As Marc Andreesen stated, "Software is eating the world". Software and technology have been eating the world for a long time. Computers have made it easy for employees to be more efficient. I think that this is great. We can make more discovers and add more innovation to the world. We absolutely need this. The only issue is that the "Creators" will be the main ones that benefit from these changes and everyone else will be left behind. So what does that mean?

What if Tesla is successful at creating driverless cars. Will the displaced taxi cab drivers, uber drivers, and chauffeurs find new jobs easily? Their skill isn't building code, designing, or running businesses; it's driving vehicles. These workers will be displaced. What if artificial intelligence removes the need for 80% of the customer service work force. Where will these unemployed individuals go? They will be displaced. I think that innovation is essential and necessary, but I also think that the gains from these new innovations will only make the leaders of these companies very rich. It's the way of a capitalist society. 

Critics wonder, "why will software displace people, while other revolutions have improved the living conditions of Americans?" I think that the Industrial Revolution and the first part of the Information Age improved the entire nation because it created low skilled jobs that lower middle and lower class could attain and also provided high skilled jobs that college graduates could attain. Blue collar workers and white collar workers were able to make enough money to buy homes, send their kids to good schools, and live a better lifestyle. The new era of the Information Age involves a highly skilled, global workforce. As low skilled jobs are replaced by software engineers and machines, job creation will fall into highly specialized areas that require higher education. Only 65% of high school graduates go to college. Of those students, very few join a STEM field.

I think that innovators should be appropriately compensated for the creativity they bring into the world. If we don't compensate them appropriately then we disincentivize people to innovate. But I also think that we shouldn't sell the story that this change will help the lower middle and lower class worker. When their job is replaced by a machine, they won't get a great severance package or new manager role. They will be displaced and forced to find a new, lower paying job. How do we make sure that this group isn't swallowed and then destroyed as software eats the world?

Want to Get Coffee

through the back door only

My schedule is pretty flexible for the next two weeks. If you are free, let's get coffee and talk. Topics of interest: 

1. Current Events

2. Venture Capital

3. Education

4. Startups

5. Techstars

6. DreamIt

7. Things to Look for in 2016

8. BCG

9. Crowdfunding

10. Music and Tech

11. Fashion and Tech

12. Exercise

13. Shoot the Shit

Back to Working Out

It's time to get back in the gym. Luckily my girlfriend provided me with a free month membership to New York Sports Club! I was supposed to get a membership 6 months ago, but I didn't want to pay the money and didn't feel like I had the time. My time was spent working with Techstars, networking, and family. That's a good focus, but I need to get myself back in balance. 

My last semester at Wharton, I took "Total Leadership". This class focuses on making sure that you are in balance. We discussed our families, self, work, and community. Each aspect is important, but generally we sacrifice one area for another. I have sacrificed myself for far too long. It's time to eat right, take my vitamins, and work out!

Accelerator Applications: Know Thy Competition

After reading several hundred accelerator applications, I've learned one common theme. Teams understate negatives and overstate positives. Personally, I like a bit of balance and intellectual integrity as it comes to applications. But founders insist on trying to "hide" things. The area that I'll touch on today is understating competition.

Why do founders and teams understate their competition? There are several reasons; most are bad. If you state that you have no competition or a few competitors, you better have put some effort into researching this fact. Let's look at the reality around competition.

If the VC/MD (...probably the associate, lol) does their own due diligence on your company and find out that there are 25 competitors, not 3 competitors (like you stated), you instantly lose credibility. One, you are too lazy to research competitors to your own company or two, you are too incompetent to do adequate research. Both realities reflect horribly on you. Just be forthright. If you have a competitive market, then STATE this and give a credible reason why you will be successful.

Just because you listed your few direct competitors, doesn't mean you shouldn't tell us about your indirect competitors. For people that may not know, direct competitors are competitors that deliver a similar product or service. Indirect competitors are competitors that could potentially enter your market and cannibalize your clientele. Understanding both of these types of competitors is key to providing a clear view of your industry. Not telling us this information is bad! We will find out. 

This may come as a shocking, counterintuitive truth, but competition in an industry is a GOOD thing. Before Google, there were a TON of other search engines. Before Facebook, there were a TON of other social networks. Those CEOs figured out the key point that the other CEOs had missed. If there is a company that actually is in a sector with very little competition, either it's a gold mine or it's a red flag. It can be worrisome because it's a sign that this is an industry where several companies failed or left the market because there were too many barriers to success. Competition generally means that innovation can be created in a proven market.

Remember, competition isn't a bad thing. Intellectual dishonesty around competition is a bad thing. You may lose credibility and miss out on an opportunity for investment. The best route is to be transparent and state your competitive advantage. 

Back to the Future II: The Year is 2015

through the back door only

The back to the future series is a classic trilogy. This movie trilogy was one of the inspirations for me becoming an engineer. Who didn't want to ride on a hover board like Marty McFly or travel back in time like Doc. 

On Spike TV, the network is playing all three movies. I turned on the channel at the beginning of Back to the Future II. If you don't remember this installment, it is based in two main time periods. Most of the movie is based in 1955, but it starts in 2015. WE are in 2015. It was funny to see Steven Spielberg's version of what the future would look like. 

Spielberg wrote this movie in the late 80s and envisioned a completely different 2015 than we have now. In the future, he had flying cars, tons of neon lights, size adjusting shirts and pants, and the infamous hover board. Our present is nothing like anyone imagined in the past. So I'm assuming that it's safe to presume that our future will look drastically different than we imagine it as well. 

What is in store for 2050. Sadly, I think it will look a lot like 2015. No hover boards or flying cars. No Jetsons styled buildings. No armageddon from terminators. We will have advanced medical procedures, better AI, and better transportation options. I'm thinking more iRobot with Will Smith than The Fifth Element with Bruce Willis. Nonetheless I'm excited for it. I'll be 60 years old by then!

NYC MTA Trains: The Epitome of Entertainment

through the back door only

Riding trains in New York is unlike anything I have ever experienced. You get a bit of everything. It's so annoying driving through NYC so everyone catches the train.

In the morning, you see young bankers, lawyers, and executives riding downtown to city hall or the financial district. The young designers, fashionistas, and VCs stop down by SOHO. The tourists stop in Midtown. Some people head uptown, but I'm not sure what jobs those lucky people are headed to; they avoid the train congestion. Outside of the regular train riders, you have the performers, beggars, singers, and etc EVERYDAY. Given this interesting assortment of people on the train, there is something hilarious to see everyday. 

Today on the train two guys got on the train blaring music from their blue tooth speaker. Now generally trains are pretty quiet, so people having loud conversations is usually surprising. So when these two guys get on the train blaring old school Usher, I just chuckled. Some people were annoyed but I was entertained. Each day I see something new. 

The coolest thing I saw on the train was a performance by some teenagers. The young performers were so good that I gave them close to 5 bucks (my average donation is a dollar). They were flipping down the thin aisles of the train. At one point, in some feat of magic, two of the performers grabbed each other's ankles and arms and proceeded to roll down the aisle together. I was pretty impressed. They did all of this in the time it took to progress from one stop to the next. NYC trains are full of interesting things and you will see literally anything if you ride long enough. 

Holiday Parties: Go Early and Meet New Friends

Holiday Parties are a great event to meet new colleagues! They are great events to get to know people and expand your network with genuine connections. These events have to be worked tactfully though. Otherwise you can waste a great opportunity. There are only so many holiday parties in a year and the Christmas Holiday Party is a staple for most companies. 

Yesterday I attended the Penn Club Holiday Party. I knew it would be a great event to meet young and old alumni that are part of the club. The younger alums provide a group of good people that are my colleagues and immediate network. The old alums provide me with a network of people that can mentor me and provide advice. This is the perfect case study around how to tackle holiday parties.  

Before the event even started I reached out to a young alum, who works at the Penn Club, and asked her if there were any notable alumni that I should be aware of or meet. If you already have a connection at an event, i.e. an event planner or coordinator, ask them if there are good people to meet. They have the inside scoop on who are attending and can introduce you to them. She stated that she would introduce me to anyone I should know once the event started. This was the first step.

I show up on time to company, club, and networking holiday parties. Most people erroneously think that it's better to show up an hour or so into the event. By the end of the event, some good conversation and networking time is over or people have left or are inebriated. Use these opportunities to meet some new colleagues and add them to your professional network. 

I arrived at the event at 5:05PM. It started at 5PM. I made sure that I was very punctual. What are the perks? The food lines are short, so you can grab something quickly. The bar is still full and no one is drunk yet. This is key because you don't want to meet new people that are too inebriated. The event wasn't too full yet. There were several spaces at tables where you could join a single alumni or a couple. I stood at a table that was near the bar and buffet. After about 5 minutes one older alum joined my table. He had been part of the club for 16 years. A few minutes later another alum that was a charter member of the club joined my table because he knew the first alum that joined me. 

Remember that older alums go to events early. Young alums generally arrive later. I was able to talk with both of these alums for about a half an hour and make an authentic connection to them. As we stood there other alumni joined us and it became a lively table. BUT I made the best connection with the two alumni that initially joined my table. We had a very long and detailed conversation. I told the charter member that I could talk with his nephew about his new startup and learned about the other alumni's 13 books. 

About 1.5 hours later, many of the younger alumni started to arrive. I knew three of them personally from previous events, so I talked with them for a while. Through these alumni, I met several other young alumni that I was able to make connections with. I ended up meeting 3 additional young alumni that were pretty cool! Many of the older alumni that I had met earlier had left by this time and the event was quickly thinning out. By the time, the open bar ended, most people were gone. 

By coming early, I was able to meet older alumni and then by staying late, I was able to connect with the young alumni. Overall it was a successful party and I met a lot of people!

The End: Demo Day

Everyone killed it....*drops mic*

That's the only way to describe how demo day unfolded. Sadly, I was up at registration for most of the show, but I could hear each of the 14 pitches. They were phenomenal. 

I equate demo day to a broadway performance. Nothing is left to chance. We practice everything night after night making sure that founders' presentations, deliveries, and body language are perfect. Founders practice in the office. Founders practice at the venue. Founders practice on the train. They even practice in the shower. Unlike broadway performances, you only get one shot to shine. 

In the audience, there are CEOs, investors, family members, Techstars alums, and friends. In the audience you can find billionaires, millionaires, and thousandnaires (that's me). This is an opportunity for companies to close their fundraising round, open their round, or add momentum to their round. 

I almost forgot about the press! The media can be a gift or a curse. There were articles in venture beat, mattermark, and several other publications. The reviews were great.

I'm proud that I ws a part of this fall 2015 Techstars class and look forward to future demo days. Here are the companies:

Flip - Making leases into liquid assets

GlossGenius - one stop shop for beauty stylists

Gorgias - Automated customer service software 

GreatHorn - Cyber security platform 

Homemade - A marketplace connecting chefs with consumers

Impact Health  - Get health insurance faster and better 

Jewelbots - friendship bracelets that girls can code

LiveLike - Sports VR

MAX - quick delivery in Africa

Morsel - Get a healthy meal at your office 

Mona - AI that helps you find clothes that you ACTUALLY want

Sailo - Marketplace for renting boats

SPIDR - next gen police tech

Slash - keyboard search 

Techie Restaurants: Panera Ordering

I was in Panera today with my girlfriend and her brother.  She did the coolest thing. While we were sitting there and talking, she ordered her food on their website and the waiter brought it to the table. He brought the receipt and the meal along with a half smile (I don't think he likes his job very much). 

I have ordered tons of food online. Some orders I have picked up at the register. Some orders were delivered to my home. But I have never ordered from my phone or computer at the table and then had it delivered to me. It's probably not very novel and can happen at many restaurants, but it was actually a pretty cool, frictionless experience.  

Then I started thinking about why iBeacon has the potential to be super help and cool along with how phones will allow for personalized orders for anything while you are in a store or restaurant. Imagine walking into a Starbucks and your phone places your custom order for you. Then the barista brings it to your table. The not so distant future is already occurring in small waves.  

Workaholics Anonymous

I don't need to attend AA meetings. I need to attend WA meetings. I have placed a large focus of my time and energy on professional success.  It's partially due to the fact that I don't have any kids yet and I live far from the majority of my family. At least that's what I tell myself.  Maybe I'll still be this way once I have kids...who knows? I like working. I like putting energy into my own ideas as well as learning new skills from traditional jobs. I read tons of self help books and educational books. I don't mind working 12, 13, 14 hour days as long as I like it and I can find some flexibility to mix in hobbies that I like.  

So I ask you and myself, is that wrong?  

My instinct tells me no but you also have to understand what is important. This goes back to your 80 year view. Most people don't care if they are remembered as a great banker or consultant or tech guru. They want to be remembered for being a mother or mentor or philanthropist. 

I have been reading a book called, "Why Should White Guys Have All the Fun." This book chronicles the life of Reginald "Reg" Lewis. At one point he was the richest Black Man in the US. He was admitted to Harvard Law without taking the LSAT or even applying. He started his own law firm two years out of law school. Then Reg eventually a $2BN dollar corporation in the 80s. This was all done by 47. He died at 50 of brain cancer two months after he was diagnosed. He had a wife and two small daughters that he never saw.  

What I wouldn't give to understand what he was thinking and feeling during those last two months. Did he have any regrets? Would he do things differently if he was given another chance? Was the personal success gratifying enough to have missed so much of his family? Maybe his actions aligned with his 80 year view. I don't know. But as I think about my own 80 year view, I hope I don't regret the actions of the young me. 

Step My Game Up

Each day that I work at Techstars, I realize how much more I need to learn. Some people are a one (wo)man show and kill everything that they do. It amazes me sometimes how skilled many of my colleagues are and how multidimensional they are. It's key to surround yourself by people that force you to step up your game. Because of this reality, I am spending my time learning more and more. 

My direct manager can create a financial model, help you design slides, edit your audio/video, and then school you on music. These skills use both sides of the brain and require bits of creativity along with quantitative prowess. I'm not quite there yet but I'm working on it. So I'm back on my continued learning and education plan.  

I join different organizations, attend various schools, and spend so much time reading so that I can polish my own skills and learn new ones. After joining Techstars, I realized how many new skill sets I still need to learn and am going to push myself to master them. Our results speak volumes about us and I feel like I can produce better results if I learn a few other things. I'll probably be back in school at 50 trying to learn something else. Who knows. But for now I'm back on the grind. 

Inside Out - A Pixar Film

This movie was another Pixar grade A quality film. I started thinking about what emotion personnel I have in my brain. Am I more the happy or angry or sad or disgusted or scared type (these were the different characters in the movie). Then I started analyzing how I felt inside and how I truly feel. 

Everyday I feel this burning desire inside to just have fun. I can't explain it. My mind and heart are telling me to have more fun and just enjoy things. These feelings especially surface when I'm super sleep, very inebriated, or bored. Maybe my mind and body are trying to tell me something. Guess I should listen. 

80 Year View

It's all about backwards planning. Teach for America (TFA) taught me many practical skills that can be utilized across several disciplines. One skill that we spent a large amount of time on was backwards planning.  Backwards planning is just as the name insinuates - you think about the result that you want to attain and then plan backwards about how you are going to get there. So if I want to buy a new car at the end of 2016, I would think about what my monthly payments would be, which lenders I would choose, and plan it out month over month.

The 80 year view is putting yourself in your future 80 year old mind and body. In this 80 year view, you look back on your life and think about all of the wonderful things you have done. You think back to your 2015 self. Remember it is 2095 in your 80 year view. Are you happy with how you did things? Did you work too hard? Did you not work hard enough? Did you cherish and build relationships? Did you care for loved ones? Did you have the right focus and mindset? The 80 year view helps you put you thoughts and action into perspective. It helps you backwards plan your life. You should do this exercise very often. It helps ground your everyday actions in what's important. The 80 year view is the long long term plan.

Practice Makes a Perfect Pitch

Years ago Allen Iverson, the Phiadelphia 76ers' star player, was confused about why the press was discussing why he missed practice in a press conference. He spent several minutes in the press conference (where he said "practice" 20 times) going through his diatribe about why they should leave him alone about him missing practice. It's a hilarious clip by the way ( - for you viewing pleasure). Sports are all about muscle memory, so the more you practice the better you become. If you look at clips of Steph Curry (23-0 record this year) this year, he attributes all of his current success to relentless practice. He makes those crazy, wack shots because he practices them everyday. 

This notion of practice plays out in every aspect of life. It affects how you perform at the job,in a sport, and EVEN at pitch events. People say, "you play like you practice" or they say "piss poor preparation leads to piss poor performance." It all lends to the same conclusion, you do better if you practice. 

Now "everyone" knows this, but most don't do it. Pitches should be practiced how they will eventually be performed. Take the time and create a great script. This could be one line for a 30 second pitch or several pages for a 5 minute pitch. As the pitches become more detailed and long, you have to make sure that you put the preparation time into the pitch, so that it comes off natural and effortless.  Steve Jobs didn't just practice his famed speeches the day before. I'm sure it took months and worked with tons of team members to create the perfect product. Perfection takes TLC and time. Treat pitches like any other high stakes deadline and you will give it the effort required.  



What to do When Everything Goes Wrong

Sometimes everything just goes wrong. First you wake up late. Then you miss your bus. You forget your lunch. Get yelled at by your boss. And finally miss the premiere of your favorite TV show. EVERYTHING goes wrong. The day has no saving grace.

These spurts of problems can occur in a day, over a few weeks, or even over several months. It feels hopeless sometimes and it seems like the negativity will never end. When we are at these low points, we have to remember that things always work out.

I always tell people that everything will workout because it must. There is no alternative to things not working out in my opinion. Maybe I'm a glass half-full kind of guy or just naively optimistic, but I feel like everything always works out how it is supposed to be. If you miss a train, maybe it was Devine intervention to keep you out of a certain situation. Blessings are considered blessings because many times we don't realize that we had received them.

Stay positive and remember that every dark moment eventually turns to light. If you feel like you can no longer do it alone, then STOP doing it alone. That's why you have a support system of friends and family. This is what therapists and counseled get paid for. This is where support groups come in handy. There are several resources that are available for you to get over this hump so never feel like you are alone. 

Life is Short...

...then you die. 

Life's s b**** then you die, that's why I get high cause I never know when I'm gonna go - Nas

Really that's all there is to say. Life is short. Do what makes you happy. Tell people thank you. Appreciate people that are important to you. This morning I had to take my girlfriend to the emergency room.  It was really scary and baffling. Occurrences like this help you refocus and put your energy back into what is important in life. Bezos calls it the regret minimization algorithm. Others say imagine if you are 80 and ask yourself if you would regret doing something you are contemplating. It all points to the same goal. Do what makes you happy. 

Ask and You Will Receive...*May Receive

Ask and you will receive is a common phrase that has been stated by people since the beginning of time. I like to adjust this statement and say, "Ask and you may receive." Sometimes your asks don't pan out. This is perfectly fine. Everyone isn't going to return your calls, reply back to your emails, or want to talk with you. BUT there is ALWAYS one person who will end up actually speaking with you on a topic. I've learned this lesson time and time again. Sometimes I feel like reverting back to my old ways, where I don't message people persistently or reach out to a random person that I don't know.  Then I remember a closed mouth doesn't get fed...and generally people want to help you eat! 

Currently I'm very interested in learning about crowdfunding. It's where I spend most of my thought energy these days. But I initially didn't know much about it. So I went to this Meetup and met a very senior employee in a equity crowdfunding space. I messaged him about connecting, so I could pick his brain about topics, and he said yes.  He ended up taking an hour and a half out of his schedule to discuss the nuances of crowdfunding with me. I also really wanted to speak with a senator about some new regulations that he helped pass in the crowdfunding space.  I emailed him. Then I emailed him again. Then I called. Then I emailed again. Then again. Finally the director at his office reached out to talk with me about the regulation.  

Sometimes you have to keep asking and be persistent. Sometimes you have to be downright annoying. Other times you have to get a warm introduction. Just keep at it and eventually the world will open up. Ask...and you may receive. 

Execution 101: Ideas are ONLY Ideas

People are always sooooo scared to share their ideas with friends, family, and strangers. There is this intrinsic fear that someone is going to steal their "great" idea. I don't want to burst anyone's bubble, but if it's a good idea and in a good space, then someone is probably already doing it and they probably have better funding.  

Mike Lazerowe said it best..."you are more likely to destroy your own company than competition. Between funding issues, founder issues, execution issues, and everything inbetween, there is a good chance you may not end up with a billion dollar company. Unicorns are hard to come by in real life and in businesses. 

The main issue with having paranoia around an idea is that it's just an idea. The process of building a actual company is 1000x harder than pontificating one drunken night in your room. The only people lucky enough to benefit off of an "idea" are the Winklevoss twins from Facebook and the long lost Snapchat founder. Be open to sharing your idea to people. It's okay. Don't give away all of the IP, trade secrets, and secret sauce, but share it enough so that people can help augment your idea and actually help you make it into a business. 

Follow Up: Scent Bird

I received my first scent bird last week. I'm really liking it. Someone did point out that it's similar to a sample size that you can get from a department store. There is some truth to that statement. There is definitely more cologne in my scent bird pack than a sample pack of cologne. Also it is sent to my house which is a huge convenience. We will see how I feel about it as time goes. Also the Versace smells really good!