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Who is Tracy Lee and what I learned from her?

The story behind my brief hiatus

Its been a while since I wrote here (about 8 weeks to be precise) - but it is with good reason. I delivered a baby girl on Feb 19th, 2015 (named her Anika :)). Hence, this short break from blogging & popups for these past couple of months.

Now I am back in the grind. I have been pondering on what topic I must first write about, on my return... and one particular topic that has been brewing in my mind for quite sometime popped up right away.

It is  about a woman entrepreneur I admire and whose journey I have been following and deriving a lot of inspiration from.

And so, with the becoming a mom of a daughter myself, what better time to celebrate and write about strong, ambitious, note-worthy women?

Who is Tracy Lee?

For the past 2-3 years I have been closely following the journey of a an amazing, dynamic, 'go-getter' woman entrepreneur named Tracy Lee.

I first came to hear about Tracy when I saw a deal for a food  event organized by a firm - Dishcrawl. Being a big fan of trying new food spots, fresh, innovative menus and new cuisines, I was very impressed by Dishcrawl's concept. To describe in a nutshell, Dishcrawl organizes food crawls similar to pub crawls. Their main focus is to get people from a neighborhood/community to get together and try out new and fun food/drink spots in their neighborhood. And in the process,  people get to know each other and the businesses get to sell/market their brand. What a fun idea! Isn't this something we would all want and like to do - whether in our own neighborhood or during a vacation? 

Except that, Tracy Lee actually went ahead and did it for all of us!

So, I was very curious and intrigued to find out for myself, about the woman behind the name and fame of Dishcrawl and (her most recent venture) Wingman.

Without any more delays, here I present, the wonderful conversation I had with Tracy. It was a great interaction due to several reasons. First and foremost, Tracy L-O-V-E-S food, and if you have not noticed, I am quite passionate about food myself. Secondly, the woman has a fantastic taste for beverages too. D-uh! @proudoenophile, wine pairings - remember? :)  Jokes aside, our conversation was also about Tracy's family, personal background, her belief system, her ever growing and driven entrepreneurial spirit!

So here you go!

Tracy Lee, CEO Wingman, Dishcrawl

Tracy Lee, CEO Wingman, Dishcrawl

Interview with Tracy Lee - CEO of Wingman &  Dishcrawl

-A fun, intelligent conversation with Tracy on topics about her personal life, her parents and passion.

Q: I have read your blogs at There is so much inspiration and motivation that I obtain from so many topics on your blog, like - "Conquer The Voice That Screams Failure And Get To Success", Get to Success looking like an Idiot and so on... 

What do you attribute to your constant urge to pursue your dreams and your amazing drive to follow your heart?

Tracy:  Part of it is just personality. I just really like to do things that make an impact on the world. I am really passionate about the projects I take on, though I'm not sure where the passion comes from - I think its just something that's inside me. I work many many hours to achieve my dreams, which I'm fine with. Part of the reason why that is okay with me is because growing up, I watched my parents constantly work on the computer during late hours. I fell in love at a young age and thought we'd be together forever. After we broke up, I was so heartbroken that I had to dive in to something to get over the breakup. So I started 3 companies and now this is where I am.


Q. In your website, there is a tag line that states:  "Finding puzzle pieces and putting them together. Maximizing serendipity". I have heard you mention serendipity in other places, interviews etc. too. What is your fascination with serendipity?

Tracy: I think what makes successful people successful is finding the different pieces around you and turning nothing in to something. Looking at opportunities in different ways. One example is, I am doing kick boxing right now. I am looking at kick boxing and thinking, do I want to pay $150 every month - no, not really (laughs). What can I do to help a business grow and help it grow my business instead of paying the $150? I do a lot of social media consulting through Wingman - so the difference between an entrepreneur and non-entrepreneurial person is, an entrepreneurial person is always thinking about something completely outside the realm of what's normal. So some people will just go about kick boxing, but I go and wonder how I can find a business opportunity. Its that type of mentality. If you take pieces from your life and find ways to maximize the connections between them - then hopefully you will be successful in some way.


Q. So, in some part do you attribute to the fact that the universe conspires for your success - if you work hard and are passionate about something?

Tracy:  If you approach life with a positive outlook or if you approach life thinking you are going to succeed, then you will. But if you approach life like 'Oh my God, I don't know if I can do this' or if you are unsure of yourself, then nothing is ever going to happen in your favor.


Q. First, you were at a job in Brocade that you quit for a great, thriving business model like Dishcrawl. Now you are CEO of Wingman - what do you say to yourself to keep pushing the envelop?

Tracy:  The key is to find out what you are passionate about. Everyone makes decisions. I made a decision that I want to go corporate, because I really wanted to make a difference. And I was very passionate about it. So I went in to Brocade and within 3 weeks when I found out that I could not make a difference, so I started 3 companies to see which would succeed. Then I focused on what I was most passionate about - and that was Dishcrawl. And I have been fortunate enough to be allowed the ability to do what I'm passionate about. Probably one of the biggest reasons people fail is because, they spend too much time trying to make the best decision. Whereas, if you just make it, you are going to either succeed or fail, and then you make the next decision. That's how you can progress through life faster and have a better chance of success.


Q. Scrappy startup, Dishcrawl or Wingman - did these ideas evolve over gradual progression or an overnight epiphany ?

Tracy: It was definitely a progression. I did scrappy startups, because I went to this event and wanted to throw an event similar to it. That sort of led me to be in the startup world. Then I was at a conference, which led to Dishcrawl, and then that took off. In building Dishcrawl, we saw a need in the market for corporations to do what we were doing. So that became Wingman. It's about taking what's working in one portion of your life and applying it to the rest of your life.


Q. What is Wingman? How is this going to impact Dishcrawl?

Tracy: Wingman is actually the parent company of Dishcrawl. With Dishcrawl we expanded very quickly and we were a consumer facing product. Through its success scaling in to multiple markets we realized that, there was also an opportunity where a lot of corporations wanted to be like Yelp and have tons of communities everywhere. So the infrastructure that we built with Dishcrawl, we started using that for other companies. In building Dishcrawl it was mostly sales & marketing - brand awareness in a local market. So we saw that there was a big need for corporations to do sales, marketing and build their brand in the local market. So we help companies do much larger scale events than Dishcrawl - to doing local focussed events. So with Wingman, corporations could want a Popup Fashion show or a beer tasting or just a huge holiday party. We focus on the experience. For example, if you want to go bowling, we see how we can elevate the experience for our clients.


Q. I have seen a lot of emphasis on your writing and interviews about empowering women and how you chose to face fear and meet success head on rather than second guess yourself. Do you have any advice for female entrepreneurs on how to go about this every time they have doubts about themselves, or their capabilities?

Tracy:  You know, we have to know what our strengths are and how to use them. So if you are really pretty and you are talking to a bunch of men, that can benefit you. I mean you should not try to hide it. We have these pre conceived notions of how we are supposed to be - but if we are just who we are, and we own it, that will benefit us. It is difficult being a woman. Even as a female we have the bias - that is just how the society works. This one time, I was talking to a male venture capitalist and he passed me to another female and I thought that was his assistant. I would have never thought that if I was passed to another male. So we are kind of perpetuating it and have to be aware so we don't make the same mistakes again. I will never make that mistake again.

Anytime you see yourself questioning something, just do it. The answer should just be YES. Anytime you feel like there is a bias, either pretend like its not happening or confront it head on. Its worse to crawl away in to a shell. Sometimes we just need to figure out what the outcome is, one way or the other. 


8. Define success.  

Tracy:  Oh, I don't know. I think success is what makes you happy. I don't think it is a dollar amount. What is going to make you happy in life? What are your goals? Not the ones your parents tell you about or what the industry dictates. But what you want to do with your life and how you want to shape it. And as long as you try and achieve that and are on that path of happiness, then you will be successful. 


We have now come to the end of the first part of my interview. Next, I asked Tracy a bunch of rapid fire questions - that only required quick, spontaneous responses without having to think more than a few seconds.


Q: If there is one thing you can eat for the rest of your life, what would that be?

Tracy: I don't know, I am foodie you can't ask me that (laughs). Dumplings, definitely! 


Q: Absolute favorite food spot in the bay area?

Tracy: Lure & Till in Palo Alto.


Q: Favorite drink?

Tracy: Jeff Morgenthaler amaretto sour.


Q: Your role model?

Tracy: My mom.


Q: Your strength & Weakness?

Tracy: Strength: My determination; Weakness: I am not as analytical as I'd like to be.


Q: Dishcrawl is a great way for people to unwind. How do you unwind?

Tracy: I eat (laughs).


Q: The most difficult thing you had to do?

Tracy: There are so many. But, I really hate firing people.


Q: If you were told you were going to be abandoned in an island and can take just one thing with you what would that be?

Tracy: My boyfriend.


Q: If Dishcrawl never happened, what would you be doing?

Tracy: Would be in another business. 


Q: One word that describes you the best?

Tracy: Passionate


So what did I learn from Tracy?

My biggest takeaway from talking to Tracy is, there are a lot of us that are being 'armchair' entrepreneurs. We like to dream, some of us even want very badly to pursue it. But, there is NO SUBSTITUTE for "acting" upon it. It seemed like, Tracy is the epitome of this sentence I once read in a book that changed my life. The sentence goes: "Life rewards action". That is right, there are dreams, and then there is action. Dreams can stay dreams or worse, be forgotten - unless we choose to act upon them.

On that note, I wish to share a video that always gives me the motivation and direction on how I see my own life's purpose - "Stay hungry, stay foolish".

Cheers! :)