7 Embarrassing Realities You Deal With As A Startup Founder (And A Bonus for Minorities and Women Entrepreneurs)

7 Embarrassing Realities You Deal With As A Startup Founder (And A Bonus for Minorities and Women Entrepreneurs)

If anything on this list bothers you, you probably should stay away from starting a business.

Starting a business is stressful, especially if you are a first-time founder. Graduating from business school, I had this rosy picture of founding a company, raising a lot of money, and being on the cover of Entrepreneur magazine.

After two startup failures and working on a third startup in 5 years, I have a few embarrassing realities that I wish I knew before founding a startup. These realities are meant to motivate you rather than deflate your self-esteem, your goals, or your desire to start a business. It’s time someone in the trenches kept it real.

1.  You will constantly beg

Whether it’s customers, investors, media, or friends and family, you will always be begging. I use the word begging intentionally. You will always be asking someone for something. Honestly, in the beginning, they will give you more than they can expect to receive.

Charity of friends and family is a natural place to start when starting a business. Humbly, with your hat in hand, you will ask your family and friends for money. You will ask total strangers to try your product. You will ask media outlets to cover your startup. No founder is above it. Even massively successful startups begged in its early days.

After Mark Zuckerberg built Facebook, he had to beg his cofounders to spam all of their friends’ emails to get their first users. When starting my athleisure brand, Rugged Black, I begged my wife to let me quit my job and work on this full-time. I begged my friends and family to support our Kickstarter. I’ve gone door-to-door with clothing samples begging retailers for consideration. If you think you can sit behind a computer and build a successful startup, you are wrong.

2.  You will do the unsexy jobs

When you are just starting a business, you are both the CEO and the janitor. That means every annoying task that needs to be done is your responsibility. It’s all hands-on deck during the early days of a startup.

The richest man on the planet, Jeff Bezos, had to deliver Amazon packages to the post office in the early days. Sara Blakely spent two years standing in Neiman Marcus hounding customers in the store, funneling traffic to her Spanx products. If you expect to only do glamourous work at a startup, please adjust your expectations.

Most of my day consists of unsexy work. I answer customer service emails, prep packages, deliver packages, clean up our stock room, and function as a door-to-door salesperson for my brand.

One of my most embarrassing moments I had was while delivering a package to a customer’s home (to save on shipping costs). The customer opened the door while I was dropping off the package. I awkwardly waved like a UPS driver and scurried back to my old, beat-up Nissan Murano. She then emailed the company address and thank the owner of the company (me) of the nice young man who hand-delivered her package (me).

3.  You will be labeled unemployed

I have two failed startups under my belt. One never produced revenue. One had less than a dozen subscribers and a few partners. My current startup, Rugged Black, produced $40k in its first two months of operation. My family and friends still see me as unemployed.

No matter how hard you are working. If you draw a salary, you are employed. If you don't draw a salary, you are unemployed in many people’s eyes. Entrepreneurship is an exercise of deferred compensation.

If your ego is easily bruised by friends pitying you or family members thinking you are crazy, you need not start a startup. There will be years of obscurity before you are recognized for your work. No one applauds sweat equity in the beginning of your startup. Quick tip: Sara Blakely didn’t tell her family or friends about Spanx for about a year after she felt the business was viable.

4.  You will look stupid

More than likely, the first versions of your products will be crap. It won’t look good. The software will be full of bugs. Something about your product will scream ‘this is a startup’s first version.’

This isn’t necessarily the case for some startups. The athleisure activewear we created could rely on the expertise of our suppliers and make multiple low-cost iterations before launching. Even though we felt good about our product, we still looked stupid.

One of our first major problems was our supplier shifted our size chart in production, which differed from the samples. Each shirt was one size smaller than what was stated on the label. We had to deal with a lot of angry customers and incurred a lot of costs for returns. The key is to minimize these fiascos through preparation. Learn from every failure, mistake, and ball-dropping moment.

If you bootstrap your startup, your product won’t have adequate enough funding to make something truly special initially. That’s why a lot of startup advice encourages you to start with a small problem, a small segment, and a small but vexing pain point. In the meantime, you will look stupid.

5.  You will be the only believer

How will you deal with obscurity? Many times, throughout your startup journey, you will doubt yourself, the idea, and your entire business. It’s natural. The reality is you have to be your startup’s Ted Lasso, your startup’s biggest cheerleader.

Even the most successful startups were started years before they became an overnight success. That means they endured years of flying under the radar, going unnoticed until they became the next big thing. The only thing that can help you get through the valley of desire is belief.

No one will care about your startup at launch. It’s funny, because as a first-time founder, I wanted to make all my friends sign a confidentiality agreement to not share my world-changing startup idea.

The journey from irrelevance is called traction. Traction is earned by working in the dark, clawing and scratching for your first customers, and doing uncomfortable things while everyone expects you to fail. Like the caterpillar being crushed in the cocoon, fighting against the pressures develops your wings and allows you to fly.

6.  You will be ignored

I send out cold emails regularly. I don’t have an extensive network of well-connected buddies in the apparel industry or a large budget to hire a PR team. One of my only weapons to gain traction is emailing.

The problem is cold emails are often (and easily) ignored. Sometimes even warm emails are ignored. If you feel awkward following up or getting on the phone to talk to the decision maker, entrepreneurship might not be for you. If I send out 50 emails, I only expect to hear back from 2-3 people. Those 2-3 people could be the start of something great.

I had an embarrassing experience while pitching the store manager at a local Denver activewear retailer. I thought after setting up the meeting I would have at least their attention during the pitch. I had to showcase our products at the checkout counter while she was helping other customers. I didn’t even deserve her attention during the previously set meeting. A lot of entrepreneurs have stories of VCs dozing off in a meeting, being stood up, or being embarrassed by a prospect’s lack of respect. It happens.

7.  You will fail

The most unfortunate reality is most startups fail. Most founders think this reality applies to everyone else. But it’s true. If you approach your startup with unhealthy optimism, this reality will be your downfall. But it doesn’t have to be. Be flexible about your methods but stubborn on your dream.

If this fear paralyzes you, please don’t apply. That’s not to say that your entire entrepreneurial journey will be a failure. The reality is many of the most successful startup founders you read in the news built their success off of previous failures.

I have learned a lot from my previous two startup failures before starting Rugged Black. I learned to manage my emotional state. I learned the value of one paying customer. How you deal with failure throughout building your startup determines whether the startup will be worth millions or zero.

8.  Bonus For Women-led or Minority-led Startups: Your “Prove-it” bar is much higher to attract funding

The reality is venture funding is plentiful, helpful, and available for promising startups. The reality is that women-led or minority-led startups have a harder time attracting funding. To do so, prove your startup is a rocket ship. As a black founder, I understand I have to be further along gaining traction than other traditionally represented startups.

I’ve been told that VCs look at four fundamental things when evaluating startups: the team, the market, the product, and traction (i.e., paying customers and growth). One of those might get you a meeting. Two will get you funded. Minority and women-led startups need at least three (with one being traction).

VC funding is not a right. It’s not fair. No one deserves to be funded. Competition is fierce. Rarely do VCs or investors invest in ideas anymore. The harsh reality is no one cares that your business is black or woman-owned. Your business has to create an urgency that VCs don’t want to miss out on.

When you start a startup, you have a limited amount of time to get off the ground before you run out of time, money, or opportunity. Hopefully, these realities will save you a lot of time and headache. Your mindset is your most important asset as an entrepreneur. Don’t let these realities trip you up.

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