Episode 107: How to be a Better Entrepreneur – Michelle Weinstein

Predictable Prospecting
Episode 107: How to be a Better Entrepreneur - Michelle Weinstein
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Have you ever wondered what it might be like to be make a pitch on ABC’s Shark Tank? Today’s guest has been there and done that, and in today’s episode, she’ll share some of what she learned in the process.

Today’s guest is Michelle Weinstein. She is the entrepreneur behind The Pitch Queen, and she’s successfully raised money and landed contracts with companies like Costco and The Vitamin Shoppe. She has 20 years of experience in sales to draw on, and of course, she was featured on Shark Tank. Listen to the episode to hear more about that experience, as well as Michelle’s thoughts on the importance of continued learning, the value of persistence, and what it means to be “professionally annoying.”

Episode Highlights:

  • How Michelle got started in sales
  • How continued learning can help salespeople improve
  • Michelle’s Shark Tank experience and how she prepared for it
  • How Michelle’s experience on Shark Tank figures into her work on The Pitch Queen
  • How persistence can add value in a sales context
  • How cold outreach can not only offer solutions to problems, but also let prospects know that they have a problem in the first place
  • Actionable steps that prospectors can take to improve their sales pitches


Michelle Weinstein

The Pitch Queen

Five-Step Pitch Queen system

Success Unfiltered


Marylou: Hi everybody, it’s Marylou Tyler. This week’s incredible guest is Michelle Weinstein. The cool thing about her is, she’s the only person on the planet that I know that has been on ABC’s Shark Tank. She’s here to talk to us today about how to be a better entrepreneur. She’s got some great years of experience, 20 plus years. She’s done a ton a stuff. She’s raised money, she’s land contracts with big clients like Costco and Vitamin Shoppe. Of course, the Shark Tank thing is above cool. Michelle, welcome to the podcast. Happy to have you.

Michelle: Thank you so much for having me. It’s an honor to be here.

Marylou: This is great. I want to know all about Shark Tank but I’m sure we want to weave that into the conversation. I’m curious, you’re a woman in sales, there’s very few of us in the planet. What got you started into this beautiful career that we love but it’s tough for women to break into. How did you do that?

Michelle: I think sales really just was maybe in my DNA. I just didn’t know it. I would say that my first set of formal training happened at Nordstrom. Out of college, I got a regular job at a company called Moss Adams. I was a financial analyst and was sitting in a cubicle for most of my life for about three years, and I was miserable. I started teaching my own boot camp classes and I got a part time job at Nordstrom. I was always buying business clothes and I said, “Might as well get 40% off and work the sales at their flagship store downtown.”

When I was there I learned that I actually had a skill just in me. I was really good. I love selling clothes to the women. I was then one of the women’s departments at the time. It came natural to me, I guess, you could say. But I really learned customer service and I really learned even more
higher level sales by going through some of their training programs. I said, “If I’m going to be here, let me see what this Nordstrom training thing is all about.” That’s really where I learned that I was really good at sales.

From that moment forward, I’m like, “How do I get out of this cubicle,” because this cubicle is not a sales job.” I was inputting spreadsheets. Actually, my nickname from one of my best friends was ‘Spreadsheet.’ She’s the comedian, her name’s Monique Marvez and she has a
whole bit about me because I do all her invoicing for her because I’m so good at spreadsheets. Literally, that’s pretty much what I did out of college. I inputted and learned formulas and this techie stuff in Excel. I said, “What could I do with numbers and with sales,” at that time. I knew I was good and up with people. Really, that’s really what it’s about. Sales is just serving

In college, I also was a cocktail waitress for four years. I didn’t know that was a sales job but it really was. When you’re a waitress selling high-end tequila shots or high-end clothes, it’s the same thing. You’re serving people what they want. That’s really what we do in the profession of
sales or if you’re an entrepreneur, you signed up for 24×7 sales career.

Anyone who’s in business for themselves, you’re selling all they wanted. I was actually talking to a mom the other day, and she said, “You know, as a mom I’m a salesperson all day long too.” I’m like, “Yeah, I guess so.” I’m not a mom but I could see it. That’s really how it all started.

Marylou: Wow, but I heard a couple of things that I want to make sure the audience also heard. Michelle, who is now the founder of her own gig, The Pitch Queen, and I’ll put her links and everything about her in the show notes. She sought out education, she definitely tried to learn more about this thing called sales, and how moving parts all fit together. She comes from
a little bit of a technical background, so there’s this idea of detail that’s woven throughout, and I think sometimes when we see this type of salesperson’s persona, they have an undeniable desire to continue learning and getting better. They definitely want to track their progress. They don’t necessarily wing every conversation, and you sounding like you have that basic DNA that
would allow you or give you permission to explore this field where you’re now teaching business owners and entrepreneurs how to do what you do.

Michelle: Yeah, and that’s exactly right. I think I’m always still learning. I even have a friend who I’ve met and we do a lot of role playing still because you can’t be the best at your craft if you stop learning.

If you want to be able to charge premium prices and you want to be able to be at the top of your game, I equate it to the top-paid NFL quarterback in NFL. That person isn’t the top-paid person because they stop throwing the ball. They actually went above and beyond and probably did more on their nutrition side. They probably did more on their workouts. They probably watched more film. They probably evolved. Whatever it was, they always worked on their game. I believe as entrepreneurs or whatever your exact craft is, we always have to be learning. I always look for other sales courses, even if I can learn one new thing from one course or one place, then I can be that much better. That’s really what this is all about.

Marylou: And you probably also put that one thing into action, to start testing it, to see if it’s something that would fit into your normal rhythms.

Let’s go to this Shark Tank’s side. Now, that is a huge thing that you have accomplished. Thinking about it, I equate it to being able to prepare, to actually pitch to a large corporation or a multi-million dollar contract, and that process of preparation. Can you tell us a little about the
history of that? How did that all start and what were some of the milestones that you took along the way that our audience can relate to as they’re trying to generate new business in their companies or if they’re entrepreneurs, to build revenue for their companies. Was there a correlation that you found in getting to Shark Tank, and if so, what did that look like?

Michelle: At the time, it was July 2014 or 2012, and it was with my last company. I was looking for my second round of investment at the time and I said, “Well, you know what? I watched the show religiously so why don’t I just apply? I think I’ll be a perfect candidate.”

I applied—and similar to how everyone here listening is probably getting ready to pitch for a new customer or grow their top line revenue, whatever it may be, you have to get prepared. I did my homework. I found every producer on Twitter and LinkedIn. I started following them. I
started engaging with them. I sent emails. I applied online and I think I hit every single angle that I got a response.

I did my first interview, and then you go to the next process, which you had to submit and video and fill out a hundred pieces of paper through the test. But if you think about getting put through the test every single opportunity that came after that for me, it was putting me through
the test.

I think everything that we do, you have to think about it as—I called my Shark Tank experience—going to the Olympics. For some of my friends that have been to the Olympics, you have to go to the trials. First, you do your regionals, then you go to the Olympic trials, and then if you make the trials, then you actually get to go to the Olympics.

This wasn’t any different and it correlates 1000% with gaining a really big client. If it’s in the multi-million dollar type contracts or any significant, large contract or customer? You can’t just wing it. You have to prepare.

I did season four and one of the others ways I prepared is, I watched season one, two, and three. I made a spreadsheet—obviously, my nickname was Spreadsheet and all I know how to use was Excel—and I documented every single pitch and deal from season one, two, and three, and studied the questions that were asked. I had all the answers; I saw the ratios as far as how much are people giving up their companies versus how much the investment was. I did so much due diligence. I ran Shark Tank pitches with my current investors I had at the time at my house and we did practice sessions with the questions, what I research from writing all the questions out. I prepared, you get to really learn, and I think for each person listening, how to be an unknown.
Honestly, when you can get comfortable with being comfortable in the unknown, which is very uncomfortable, then that’s where I think a lot of magic is created.

That was the Shark Tank experience, pretty much from July whenever, I taped, I probably applied three to four months prior, and every time they hang up the phone with you, they say, “We’ll let you know what the next step is and just know that there are no guarantees.” Every single call and email, that’s what you would hear, “Just so you know there’s nothing guaranteed. Just so you know, you might not hear about from us.” It was nuts to even think that that was even possible and they say until you see yourself on TV, then that’s when you know it’s real.

Here’s the funny thing. Well, now it’s funny, at the time it wasn’t. One third of every single taping, doesn’t air. If they had 140 […] actually pitch and tape. Prior to that, they send people home because you have to pitch to the producers prior. If you don’t pass the producer pitch then you get sent home.

So, there’s the regionals, there’s the nationals, there’s that Olympic trials, and then you get to go to the Olympics and not standing in front of them. At every moment you can get cut. There was about 40 of us that got this email that says, “I’m so sorry but those of you with deals and no deals, unfortunately, your episodes will not be airing this season, and we’ll let you know if it does in the future.”

My episode number aired after all of that but I said that experience is what helped me with my last company. I pitched to Vitamin Shoppe a really outside-the-box idea to really change the supplement industry to more of a preventative approach, and we were able to do a 10-store test inside Vitamin Shoppe. I was meeting the CEO of a multi-billion dollar company. That experience of preparation for Shark Tank got me prepared for anything.

So, I got into the Vitamin Shoppe. They invested over a million dollars in a project, it was great at the time, and was able to pitch to buyers for Costco with my products. I did a lot of B2B business. All I can say is thanks to the Shark Tank experience that got me prepared for being
uncomfortable, being comfortable, and being in the unknown.

Marylou: But also, as you said, the thread through this is at each step you earned the right to actually go to the next step. When we look at prospecting and we break it down into the steps of prospecting at the various stages in the pipeline, which is what I teach, it’s all about what you
need to do at the step you’re at in order to earn the right to either go to the next step in the active pipeline or put them to sleep for a while because they’re not a good fit right now, or actually get them out because they’re definitely never going to come back into the active pipeline. You’ve set that stage that each step is important, each step has meaning, and each step earned you that right to go to the next step. It’s so great that you had that experience.

Let’s take that experience now and let’s focus on The Pitch Queen. What aspects of the Shark Tank or that experience do you instill now in your troops? In your business owners, entrepreneurs, and people who love to work with you, where do they start? Is there a mountain they’re climbing or do you spoon feed them with the various pieces of information that they need in order to skyrocket their revenue?

Michelle: Mostly with what I do today with The Pitch Queen and the brand—obviously it’s a lot of sales, but primarily, people that are selling a really high ticket offer, a high-value service. I work with a lot of certified public accountants, CPAs, that have clients that are doing services of anywhere from $3000–$10,000 every month in revenue or maybe one-time engagements of
$50,000–$100,000, what is that process of selling and building that relationship with that type of client, and how do you service that type of client at that level. That’s really what my main focus is. It’s really on the high offer, high value service process of selling.

I would say that The Shark Tank experience and how it correlates in what I teach today, is really about persistence. I teach a skill set called being professionally annoying because, for everyone listening, you all know how much you have to follow up. But if there’s someone you really want
to work with, there’s really great ways on how you can follow up and how you can do it in a professional manner. I would say that even The Vitamin Shoppe or Costco or anyone that I’ve worked with in the last eight years, they say that that is the quality that I have and now I teach it to people.

I think a lot of times we might be feeling this too in the beginning stages of when you are selling or starting your business. You don’t want to annoy people. You don’t want to be, not only annoying, but you don’t want to bother them. Well, to be honest, if you’ve got something great or you got a solution to a massive problem and I believe that every single thing I do today or the clients I worked with, you have to have a significant solution to a massive problem. If you don’t follow up or you think you’re bothering them but you have the solution, then you’re actually doing them a disservice, or you’re doing that company a disservice.

If The Vitamin Shoppe told me, “We really want to be different that GNC and everyone else,” and I had these fresh prepared meals, and I was 1000% that this would differentiate them. I knew that I could execute and make this big, huge project happen. If I didn’t follow up, they would have actually never worked with me. But they told me that because I was so persistent, that’s why they chose me over three of my other big competitors at the time, that were much larger companies than us. But they knew that because of my persistence and because of my willingness to pretty much go above and beyond, that that’s why they chose me and my company.

All of that is in me but it even got a lot deeper with the Shark Tank experience because if I didn’t follow-up and wasn’t persistent, guess what? I probably wouldn’t even have made it past August. I probably would have never even have had a taping. They want people that are hungry. But you
can do it in a professional not annoying way, that you’re not bothering people, and that you’re actually there to wake them up. If you don’t wake these people up then you’re actually hurting them by not being persistent and following up. At that time with my food company, I was here to change lives one meal at a time.

So that was my mission and you obviously have and mission and a passion that correlates with it, but that’s what helped everything and how I was able to get a lot of those B2B deals done.

Marylou: As part of that, we’re getting drilled ad nauseam in our world about adding value for every sales conversation that you had, but there is no definition of what that means, adding value, adding value. Being professionally annoying is also adding value because each conversation that you choose to have does something so that the prospect recognizes that, “Wow, this is different. This is something that I want to learn about, get to know, have more conversations around.” That blueprint that you’re teaching your clients, what I call patiently persistent or pleasantly persistent.

Michelle: Yeah, or I call professionally annoying—they’re all the same thing.

Marylou: Professionally annoying. It’s all the same. But I think having that framework of what exactly does that mean and how do I link conversation to conversation, especially if I’m top of funnel, where I’m starting more cold conversations in my world—we do targeted outreach—so we’re trying to start conversations with people we don’t know. I too have had that same experience as you, of people saying, “Oh my gosh, Marylou. Thank you so much for continuing this conversation. I don’t think I would have found you had you not reached out to me.”

Michelle: Sometimes people don’t think they have a problem. If that’s what I think it is, even with the people that I work with, certified public accountants, a lot of them don’t think they have a sales problem. Why would they go look for you if they didn’t even know that they had
a problem? But if you open up their eyes to the possibility that maybe, for my CPAs, why their business isn’t over a million yet, well, a million in revenue means you need to increase your sales. If, you have a problem in your sales process or you just keep answering people’s crises, or when a client calls, say how much do you cost and you just give them a number, that’s a problem. But they don’t even know that that’s a sales problem.

Marylou: Exactly.

Michelle: For all of you who are doing some cold outreach, just remember, they don’t even really know if they have a problem.

Marylou: They don’t. They’re unaware, like you said, they don’t know that they have a problem. They think they might have a small problem but they have no idea where to look for solutions. There’s five levels of awareness that we have to be prepared for in that sales conversation in order to be able to get them to bubble up.

The other thing I found, is that we don’t define who we are and why we matter well enough in these conversations, so value is also about you. It’s about why people should change what they’re doing now and start having a conversation with you. It’s not all product-related at all, really at top of the funnel.

Michelle: It has nothing to do with product.

Marylou: Yeah, exactly.

Michelle: It all has to do with relationship and the rapport that you build with the person because we all know that people buy from people. If it was about the product, Vitamin Shoppe would have never worked with us. Granted that we have a great product, but they were buying the person.

Marylou: Exactly. So in our parting comments, I want to be respectful of our time with our folks. I’m going to put all the information of how people can reach you, on your page or website but let us know, tell us in parting what are the two or three actionable things that people can start today, after listening to this podcast? I heard planning, planning is one.

Michelle: Planning yes. Also, take one thing that’s been on your to-do list and go do it, or one thing that you’ve been wanting to work on in your sales skills and actually implement it, not just talk about it.

Marylou: Definitely. And then, you have a framework. You have a way of getting people to uncover this value. How do you spread out this value and become professionally annoying, but do so in a way that you have reason why to contact them multiple times.

This is the biggest problem that I see. People are afraid to contact because they are “annoying,” but you’re not annoying if you are adding that value. But what does that mean? That definition of value, I think, that’s where your methodology would really help audiences like mine. But we’re
starting these conversations, we’re trying to build the relationship first before we start talking about product, feature, benefit, and results. We used to talk about results but we do it in a very emotional way to get people curious, fascinated, asking us, “Well, how do you do that?” and I think that that’s where, from what I heard in this conversation, you really excel in getting your folks to start moving in that direction.

Michelle: Yes, for sure. I have so many worksheets and different things that you guys can use but I would say the best way is to go to sellwithoutsleaze.com and you’ll get my Five-Step Pitch Queen system, and I do cover this thing called professionally annoying. If you go to sellwithoutsleaze.com put in the best email address, you’ll really be able to hopefully boost your
confidence in the conversations you’re having with people but also again how you bring value to them.

Like you said, it’s all about value but for each person listening, each have a different product but just think about the human connection. It’s all about the human part of it. So hopefully, that will really make a big impact.

On my emails, I send out also two a week. One for my podcast called Success Unfiltered, and then one from my live show. I do a Facebook live show. I also record the audio called Coffee Is For Closers. I think I did a whole month of following up and exactly on what we just talked

You’ll be able to see that and again just go to sellwithoutsleaze.com, put in your best email and you’ll get my five steps system that really take the stress out of selling for good but also really build that confidence.

You can also listen the whole month of the follow-up. The art of the follow-up. But just take one thing and do one thing because like you said earlier, if you don’t put anything into action, then you’re not going in the forward direction. You can listen to me, you can listen to every single
guest here all day long, but if you actually don’t implement, then you’re not doing yourself any good and you’re not doing your clients any good.

Marylou: Exactly. Amen, Michelle. Well, thank you so much for your time. I will put all these links on Michelle’s page so that you guys can get over there. I would definitely download that five-step process because that’s going to get your started thinking about chunking down those
conversations into multiple steps are you’re working through the pipeline, from that initial conversation through the following-up sequences, and then on to the opportunity stage.

For us it’s a must-have type of framework, so that you can craft the right conversation for each of the different people that you’re selling to along the way. As you’re moving these accounts from that first stage all the way through to opportunity, and then beyond, which I don’t cover, but Michelle probably covers all the way to close but you have information going on there.

Wonderful. Thank you very much for your time and we will be sure to put all these links for everybody.

Michelle: Oh, thank you so much. It was an honor to be here. Thanks again.

Marylou: Okay. That’s a wrap. How did that feel for you? That was great. Really good.

Michelle: Good. Awesome.

Marylou: Awesome tools and things that you put together. It’s so great, I love it.

Michelle: Oh, thank you.

Marylou: What I do is I have The Pitch Queen—

Michelle: Or email the stuff for when you’re in town, too.

Marylou: Yes, I’ll get that over to you right away.

Michelle: Because I want to put it in my calendar.

Marylou: Yeah, and if there’s any special links you want me to include, if I go to thepitchqueen.com, there’s the links to a lot of these other places, but I’d like to give them the
list of the links that are there, that you want to look out like the, Sell Without Sleaze, the Coffee Is For Closers, are those all different websites?

Michelle: No. The Coffee Is For Closers page is on my website. The Sell Without Sleaze is the only one and then the podcast page. If you want, I can just send them to you right now.

Marylou: Yeah, let’s do that so I have it I can send it off to my team so they get this thing ready. They put the page together and stick it out there on my website, in iTunes, and wherever else it goes. Very good. So, I will send you—

Michelle: And then just let me know when it goes live and we’ll share it out for you.

Marylou: Yes, I’m running about a month behind now, it looks like end of May-ish, somewhere around there, I’ll have a better idea. As I look through the schedule, but I think it’s around end of May, early June at this year.

Michelle: Okay. Perfect.

Marylou: All right. Thank you so much. I look forward to hopefully seeing you in person.

Michelle: Thank you. Yeah, please. Send it.

Marylou: I will. Take it easy, Michelle. Thanks again.

Michelle: Alright, bye.

Marylou: Bye.