Two days before my dream business was slated to open, a confession of almost a decade of cheating rocked my world. Instantly, I became a single mother and entrepreneur. I had no investors in my business or venture capital guys lining up to write checks.
Additionally, as a stay at home mom, I had no income or assets to call my own. Like many struggling entrepreneurs, I began each day with zero guaranteed dollars in my account. Exhausted and hemorrhaging hope, I eventually found the key to starting a business broke: the willingness to do uncomfortable work, or in other words, wear unpleasant hats.
One hat I love to wear is being mom to these two guys!
Wearing a hat means placing one specific task in your crosshairs at a time and executing. Typically the tasks associated with these hats are given to someone else to undertake. When budgets are big, these roles are delegated or outsourced, allowing owners the time to stick to specialized work. When your pockets aren’t so deep, however, it is time to roll up your sleeves and put on a hat yourself. Time yields money when it is devoted to generating business. It’s not glamorous or complicated, but wearing the hats of hustler, lobbyist, and salesperson are mission critical when your bank account is lacking in commas.
Hat #1, Hustler: Start Strong and Start Lean
Exactly how do you start a business broke? The traditional model begins with a business plan, proven concept, skin in the game, and relationships that you neatly assemble to pitch to investors.
Perhaps you’ve done that or maybe lack access to individuals with extra cash to invest. In any case, consider the decidedly gritty route of becoming your own VC investor. Start strong and self fund by being a certified hustler.
Gasp, you respond, the blood rushing to your face. I am starting my business because I need money and now you are suggesting I invest money I don’t have? Indeed.
Hustle to Make Money
An unusual goal requires an unusual way of thinking, especially when you are broke. Wearing the hustler hat means looking for or creating work that is profitable but not visible. The concept of hustling is not a new one and nearly every self-made person has worn this hat, although few talk about it.
As a point of reference: KFC’s Colonel Sanders himself was a steam engine stoker, insurance salesman, and filling station operator. Meghan Markle (Duchess of Sussex) wrote calligraphy for wedding invitations. Having a second or third job is an honorable way to finance a dream.
Good luck finding a small business line of credit when you are first starting. The application process can be tedious and if granted it’s as though you are making payments on your own idea. Mark Cuban once boldly proclaimed, “Only morons start a business on a loan. … With so many uncertainties in starting your business the only certainty is paying back your loan.” But I think my mechanic said it best: “It’s amazing what you can buy with the bank’s money.” In other words whatever the bank loans, it owns.
If $10,000 to $20,000 would make a big difference in your business, you might be surprised at how easily this amount can be obtained by a decent hustler. Look for work that pays quickly, often in cash, and is clean cut. Have a special skill? Teach lessons. Drive a car? Hire yourself out. Able to work nights? Become a server. At a decent restaurant in the American Midwest, a server can pull in over $200 in tips on a Saturday.
A fun, go-to side hustle for me: giving tennis lessons.
Being a hustler kept the lights on and brought me out of a nearly impoverished reality. Every single day I stopped by Goodwill stores to flip home goods like mirrors and wall art. The stores became my ATM. Buying items for $5 and selling them for nearly $20 online is powerful. Not much beats a 200% cash return on investment in less than a week.
The second thing all hustlers know is how to start lean. Begin your business with the smallest amount of overhead cost.
Spanx founder Sara Blakely’s HQ was her home for years. Dwayne “The Rock” Johnson slept on a used mattress from the garbage behind an hourly sex motel during his hardest times and Tyler Perry lived out of his car. Hustlers do what is needed to make ends meet.
If you can limit your costs, before you know it your dollar will be doing yoga and stretching to the max. There are countless ways of to start lean.
- Set up your business in a shared co-working space.
- Attend free mastermind sessions administered by your local chamber or city group.
- Recruit interns to do work you are not skilled at or do not have time to do.
- Create trade relationships where you receive perks you’d be willing to pay for if you had the money. Sports events, concert tickets, advertisements, jewelry, and even hair styling are great trades as they help eliminate costs in helping you show up professionally and entertain clients.
- Pitch your business problem to an MBA class they can take on as a graded project. Think of it as free consulting as bright students devote class time to finding a solution to your issue. They receive a real world learning experience and you get valuable insight that didn’t cost a cent.
Once as a consultant I literally worked on trade for meals. Working for food sounds like a dire situation, but in my mind, I had a personal chef.
Mentality is the key to fully maximizing this hat. Hustlers’ minds are always crunching the numbers, figuring out how to get things done and owning the results. The hustle mentality is cultivated by the need to succeed. Monetize every moment of your day and wear the hustler hat with pride. As Gary Vaynerchuk says, “What I’m completely convinced of is that I don’t think people can outwork me.”
Hat #2, Lobbyist: How to Get Anyone in the World to Respond to You
Oprah Winfrey. Quincy Jones. Daymond John. Bill Clinton. Disney. What do they have in common? All of them have responded to me in one way or another.
Me and Gayle King
A lobbyist is defined as an activist that seeks to persuade. Cold calling for donations on behalf of a teen pregnancy home (as a teenager myself) helped cultivate my own lobbyist hat. You quickly learn what it takes to get past gate keepers and how money will not make people respond to your request. The only thing that will help you is chutzpah.
The first thing to know about lobbying is that persuasion benefits both parties, while manipulation only helps one. It is important to keep this fact in mind when trying to influence. When attempting to connect with a contact, think in terms of your added value in addition to the benefit you’ll receive.
During my time as a consultant for emerging businesses and brands, I cultivated my outreach technique that I named, “The High-Low-Circular Method.” This method is so effective that I’ve been asked to give talks on it. Some responses can take up to six months, but I’ve often seen same-day results. The length of time depends on the accessibility of the targeted contact and the diligence of the entrepreneur. No one can advocate for your business like you. So put on the lobbyist hat by identifying an individual or business to get in touch with, clearly know your ask, then go High-Low-Circular.
Write the name of your dream contact on a piece of paper. Stop and think of how to get in touch with them directly, this is called High. Going High can mean finding an email address or sending a direct message through a social media app. Sometimes it means being bold by cold calling and asking to speak to your contact.
Consider attending a conference or speaking engagement promoted by the contact and meeting in person at the event. When introducing yourself in person, remain calm and say what you do in a six-word sentence. One thing to keep in mind, overeagerness communicates desperation and will not be taken seriously. Also do not publicly @DreamContact just yet. This is a last resort Hail Mary tactic.
If nothing comes from going High then look at the company’s LinkedIn page and select “People.”
On the piece of paper under the contact write down the names of those that are “Low” ranking within the organization. Previous employees and interns are listed on LinkedIn and are typically happy to point you in the right direction.
Request to connect with people who can give you answers. Once connected, ask who the correct person to message your request or invitation to is. If you are looking for a way to layer your outreach, consider inviting them to an event. This type of invitation can be for a community project, a performance, or a launch. Event invitations are an excellent way to get responses from well known contacts, as no one on their team wants to be the person who did not deliver an invitation. An invitation can sometimes push you to the front of the line of people trying to make contact.
During this stage, it is vital that messages are no longer than three sentences. Here’s a sample email script:
Subject: Hi Suzanne
Hi Suzanne, congrats on your community work raising money for X charity and thanks for the add on LinkedIn! Looking to get in touch with Billy X to invite him to an upcoming event. Who is the right person to message?
The top mistake that lobbyists make is length, their initial messages are just too long. As a rule, if the message requires the reader to scroll down, it will not be read.
Now draw a circle around those names with your targeted contact in the middle. Who are the people that are connected with the contact but do not directly work with their organization?
This can be found by searching online, reading articles, and looking through social media apps. Often these are friends, associates, nonprofit organizations, and fellow businesses. This is the circular stage of the method, where you make connections with those identified on the outer circle.
By becoming part of the outer circle, the contact in the middle will begin to hear about you. Ideally, by the time this happens they will be inviting you to coffee, as they can’t believe they are the last person to meet you. The circle phase takes longer, but is extremely effective, as it feels more organic once connected.
Wearing the lobbyist hat pays off with two things that are not always for sale: influence and access.
Hat #3, Salesperson: Ask and Ye Shall Receive
“Nothing happens until someone sells something,” is a popular quote attributed to Henry Ford, Peter Drucker, and Mary Kay Ash. Who ever came up with it couldn’t have put it better.
As the first person to believe in your idea, you must be the best salesperson to get it off of the ground. Telling your story and sharing your vision every single day will get you ready for the big moments of pitching to investors or selling your idea to potential clients or business partners.
What good is an idea if no one knows about it? How valuable is your product or service if no one buys it? Wearing the salesman hat requires the passion to ask such questions and keep asking potential clients until their answer is “that’s right” and “yes, I’ll take it.”
Knowing there are two salespeople in every conversation is the secret to the sales hat. There is the person who is selling a product or service, and the person who is selling a “no” answer. If no is accepted then they were the better seller that day. The best communicator is one who asks the right questions. Starting a business broke is more about knowing these questions than having all of the answers.
Asking questions is the most important skill to sharpen when selling your business and ideas. Questions are key because whoever is asking questions is in control of the conversation. By mastering all facets of questioning, including who, when, what, and how, you’ll learn to get what you want in ways that money can’t buy.
Who To Ask and When
Asking the right questions to the correct person is step one. Your why will inform you of who to ask, just as you experienced with the lobbyist hat. Tailor your questions to the person you are speaking with. Is your contact a gatekeeper or decision maker? Posing the proper question to the right person will have the greatest effect. If you are dealing with gatekeepers or networkers, consider asking:
- “Who do you know that can X?”
- “How can I get in touch with Y?”
- “What does it take to Z?”
One overlooked factor in successful asking is when. In one 2011 Princeton study, offenders were more likely to be granted parole after a judge ate a meal. This particular finding has since been disputed, but there’s an intuitive lesson here—timing matters. We learned this back when we were kids hoping to get on our parents’ good sides before asking for something.
For a favorable outcome, try to schedule meetings right after a meal. Avoid setting appointments right before lunch or at the tail end of the day, especially on a Friday evening. To increase chances of success, have the meeting over a meal and then discuss business after the food arrives.
What To Ask
At the start of all sales transactions, ask, but most importantly listen. “What are you looking for in…?” is the best way to find out how to present your product. When I was a Division I head tennis coach and recruited athletes from around the world, the top question I led with was: “What are you looking for in a Division I university?”
The prospective student-athlete would answer: “A team that feels like family.” Cue a family answer, “Well, we have team dinners once a month. We often go to movies and we have a beach on campus. It is a real family environment here. Your teammates are all from different countries, so at the end of four years it is like you have family members around the world.”
On the other hand, if her answer was, “I”m looking for a strong business school, all about academics,” my response is different. “US News and World Report ranks our business school as one of the top in the nation. We have mandated study hall each week to help you stay focused and our team GPA is the highest in the department. We are committed to academics.”
Same school, different sales pitch. Leading the sales transaction with questions and then modifying the answer based on what you’ve heard leads to success. Let their answers be your guide.
How To Ask
Steer clear of Why questions, as they make people defensive. Stick with How, What, and Who. In Michael Bungay Stanier’s book The Coaching Habit, he lists several powerful questions that can transform any conversation. A few that can lead to successful sales include:
- And what else?
- What’s the real challenge here for you?
- What do you want?
- How can I help?
The stage has been set, intentional questions have been asked of the right people at the right time, and now for the finale, the close.
Closing the sale or asking for the sale can feel like a negotiation. The key to no longer being broke is how efficient you can be at closing, aka getting paid every cent you ask for.
“Never split the difference,” is the advice of former FBI hostage negotiator Chris Voss, as he says in his book by that title. His “field tested tools for talking anyone into (or out of) just about anything” are worth every penny for entrepreneurs. For example, by asking, “How am I supposed to do that?” it triggers the process known as “reverse empathy.”
According to Voss, “Reverse empathy is used to put the other side in a position where they have to take a fair look at your position. It makes them think things through.” By closing the sale with specific questions you’ll get clients to think about how to solve your money problem empathetically.
‘The Power of Broke’
Daymond John coined that phrase, and it’s real. Be encouraged if you are broke. The entrepreneur mindset required to wear different hats is the activator that leads to generating money. And remember that starting a business without money is a temporary status.
Be inspired knowing that there are thousands of fellow founders around the world that are bootstrapping their businesses without funding. Not everyone was born with a silver spoon in their mouth, but by wearing the hats of hustler, lobbyist, and salesperson, you’ll be able to grab yourself a straw.
How has not having enough money affected your business? What solutions have you used to overcome being broke? Which hat do you find yourself wearing most? Let us know in the comments below!