An Entrepreneur’s Tips To Planning A Wedding

Posted by on Jan 31, 2014 in Uncategorized | 0 comments

I’m going to take a break from my usual topic of entrepreneurship to talk about an unlikely comparison: wedding planning. As entrepreneurs, we have to learn to balance being obsessed with our businesses and dealing with all the other stuff (life). With limited time, we must make sacrifices and learn to make do whether it’s with limited resources in the business or limited attention to big things like a wedding.

Now when I got engaged, it felt like a big heavy weight was placed on my shoulders. A very pleasant and exciting weight, but nonetheless a heavy burden. I decided to employ some of my hackerish startup ways in my approach to wedding planning. For those non tech-inclined, a hack is just a way to get seek efficiency through bucking the status quo- it’s a way to get something done with spending fewer resources (time/money) than allocated.

Now, if you’re like me, you have no interest in spending hours on Pinterest perusing cardstock for wedding invitations and learning how to sew a wedding dress. If you’re like me, you want things done tastefully at your wedding, but don’t have the luxury or inclination to try to save a few bucks by taking calligraphy classes to address your own invitations.

If you’re like me- you want a fantastic wedding, but you don’t want the drama or stress involved. Here are a few of my own hacks:

1) Consider A Wedding Planner- Many people think wedding planners are expensive and only for rich people. Newsflash: My wedding planner has saved me so much money, he has paid for himself many times over. Why? The wedding industry THRIVES on information asymmetry- since you’ll (hopefully) only be planning one wedding in your life, you just don’t have the necessary information about what prices are legitimate for services. Vendors do an amazing job about being completely obtuse when it comes to pricing.

My wedding planner has done over 500 weddings; all I need to do is shoot a quick email or text and get 500 weddings worth of data- this makes my decision making process faster and easier. Also- all those moments popular media show bridezillas stressed out? Say so long sucker to that feeling when you have a wedding planner. Whenever you feel overwhelmed, you have an expert to ask.

One final note on wedding planners- many have different packages with varying fees. Hiring a wedding planner does not mean you won’t have any input on your wedding day. Essentially, packages are designed to give brides the amount of support they need, whether it’s 100% planning or just someone to be there the day of to coordinate. Our package was somewhere in between.

English: A bouquet of flowers.

Your wedding can be a bouquet of originality: be true to your relationship.

2) Delegate- When we got engaged, my fiance and I decided that our wedding planning would be just like our relationship- 50/50. While I tend to have stronger opinions in some cases, my fiance also has strong opinions in others. Wedding planning is assumed to be a bride’s responsibility, but that is what you make of it. Vendors tend to speak only to the bride (in my experience) but they will always respond in the affirmative when the groom is just as opinionated. Just like in my businesses- I’ve learned to let go of certain tasks that others can do better.

For example, I put my mom in charge of flowers because that is her passion and I have little opinion on the matter. Hydrangeas, orchids, carnations- I couldn’t tell them apart unless I could do a [entity display="Google" type="organization" subtype="company" active="true" key="google" ticker="GOOG" exchange="NASDAQ" natural_id="fred/company/1821"]Google[/entity] image search. Do what you love and delegate the other tasks to your groom, family and bridal party.

3) Outsource- When we ordered Save the Dates, they came in the mail without addresses on them. Doh! I totally forgot that we’d need to address the actual postcards. My initial thought was to just do it on my own, but then the mental image of a very inky pinky and chicken scratch handwriting came to mind. Instead, I headed for one of my favorite timesaving websites: TaskRabbit.

I hired someone to address and stamp all of my Save the Dates for only $75. This would have taken me hours to do myself and the result was way more professional and elegant. In life, I believe people should do what they do best and enjoy doing- for me, that is not many of the things associated with wedding planning. I let the professionals step in and trust them because they wouldn’t be professionals otherwise. New startups like Brideside are also popping up to capitalize on bridal inefficiencies- such as accommodating bridesmaid dresses for bridal parties scattered throughout the country.

Just like in running a business, planning a wedding can be overwhelming, frustrating, and incredibly expensive. However, just like running a business, everyone has to follow their own ideas of success and understand that the industry exists to accommodate everyone’s needs.  Your business is probably not the next Instagram, and your wedding is probably not as “perfect” as the Royal Wedding. But guess what? It’s your business to run as you see fit, and it’s your wedding to do whatever is true to you.

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This Is The Right Time. This Is The Right Opportunity.

Posted by on Oct 1, 2013 in Uncategorized | 0 comments

So many times in my life, I second guess decisions. Am I doing the right thing? Are there better opportunities out there? I’m guessing I’m probably not the only one (read: female) who tends to overanalyze whether what I’m doing is the right thing, right now.

What happens though is that looking back, I never really regret the choices I’ve made. Every opportunity presents ample learnings and I become a better person (at least I hope so!) having gone through it. Now, I constantly remind myself…

…This is the right time. This is the right opportunity…

Serge and I are ambitious and we want to accomplish a lot of great things in life. Sometimes it’s really easy to get ahead of ourselves and compare our achievements to others in our peer group. That’s when the mantra above comes in extra handy.

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6 Ways Entrepreneurs Lie To Themselves

Posted by on Sep 30, 2013 in Uncategorized | 0 comments

(This article was originally posted in Forbes)

There’s a learning curve in the entrepreneurial world, and sometimes, it’s easy to tell where someone is in their  journey just by the way they talk. Both of my companies (matchist andEntrepreneurs Unpluggd) targetentrepreneurs, so I tend to hear the same few phrases and ideas over and over again.  Here are the most common, overused phrases that you should absolutely avoid when talking to others about your startup:

“I can’t tell you my idea. You’ll need to sign an NDA first.”

Variations: I can’t share my idea, I’m afraid the developer will steal it/ Don’t share your idea with other people, they’ll steal it/I’m operating in stealth mode


What you’re really saying: “My idea is so special and secret, if I tell you, I think you’ll drop everything you’re doing and run off with it.”

Why entrepreneurs say this: When entrepreneurs are starting out, all they’ve got to hold on to is their idea. It’s what fuels their passion and ambition.

What experienced entrepreneurs/investors/advisors think: This is the sign of a true novice. Serial entrepreneurs know that it’s never about the idea, it’s about the execution. At the early stages of a startup’s life, every time you don’t tell someone about your idea, you’re missing out on the opportunity to find a customer, partner, or advisor. It’s obvious not to share proprietary information like algorithms but if all you’ve got is “I’m building Facebook FB -0.3% for dogs,” there is no need for full secrecy. In fact, famous VCs have made clear that they will never sign NDA’s as it’s a terrible way to start off a relationship.

“I’m looking for a technical cofounder.

Variations: I’m looking for a developer who will work for equity

What you’re really saying: “I want someone to work for me for free.”

Why entrepreneurs say this: The mythical technical cofounder is half of the hacker and hustler dream team. Unfortunately, entrepreneurs who are in search of a technical cofounder often put their project on hold rather than validating their assumptions through non technical means like making sales or building an MVP using a spreadsheet or landing page.

What experienced entrepreneurs/investors/advisors think: You’re likely overlooking a lot of work that can be done while you’re searching for someone to join your team. In fact, you can always hire a dev shop or freelancer to help build an early version of your product. What most entrepreneurs realize is that for the majority of businesses, the technical part is easy- customer acquisition is the hard part.

“We’re crushing it!”

Variations: We’re kicking ass/We’re killing it

What you’re really saying: “We’re still around and figuring it out.”

Why entrepreneurs say this: There is a veil of expected success around the startup world. Entrepreneurs fear appearing weak or vulnerable because TechCrunch and media outlets consistently feed success stories, fundings, and acquisitions.

What experienced entrepreneurs/investors/advisors think: A serial entrepreneur knows there is no such thing as “crushing it;” even when you’re doing well, you want to be doing better.

“A few VCs have shown interest in my startup.”

Variations: I’m currently in fundraising mode/ I’ve got a couple of angels interested in the company/ A few VCs have said they’ll write big checks.

What you’re really saying: ”Someone who has money took a meeting with me!”

Why entrepreneurs say this: Entrepreneurs think investor interest is a sign of validation. What they don’t realize is that investors will almost always show some sort of interest because they’re scared of being wrong (read this story about the fund that passed on Twitter).

What experienced entrepreneurs/investors/advisors think:  Investors will almost always show some sort of interest because they’re scared of being wrong (read this story about famous passups) and they’re largely driven byFOMO (the fear of missing out). They will string entrepreneurs along as long as they can: usually they will invest when others are putting money in or when they have to say no. Interest means nothing, in fact only a term sheet or check means anything.

“We’re exploring a few different pivots.”

Variations: We’re considering a pivot/We’ve discovered new opportunities

What you’re really saying: “We have no freakin clue what we are doing, and we are trying to figure it out ASAP.”

Why entrepreneurs say this: Startups are about failing quickly and finding product/market fit as soon as humanly possible. Entrepreneurs typically try to pivot when what they’re doing isn’t working, or when they stumble upon a different idea/concept that has more potential.

What experienced entrepreneurs/investors/advisors think: This is both good and bad. The entrepreneur understands that most of the time, the original idea is not the one that will succeed so it’s good to be flexible and experiment early. However, it’s a sign that poor research may have been done early on before seeking investment and/or building an initial product.

“Monetization? We’ll figure that out later.”

Variations: We’ll grow our user base then monetize/We’re not worried about monetization

What you’re really saying: “I’m building something that is so cool I don’t have to worry about something so dirty as money”

Why entrepreneurs say this: One word: outliers. You can think of a few companies that followed the “users first, monetization later” strategy and hit it big (Facebook, Twitter, Instagram).

What experienced entrepreneurs/investors/advisors think: While this strategy works for outliers, thousands of startups fail because they don’t think about how to monetize their products early on. As Professor Waverly Deutsch of TheUniversity of Chicago Booth School of Business likes to say, “It’s not a business until you make enough money to get paid. Just a hobby – a very expensive hobby.”

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How Honesty Can Save Your Startup

Posted by on Aug 29, 2013 in Uncategorized | 0 comments

(This was originally posted in Built in Chicago)

Yesterday, former Chicago entrepreneurs (they moved out west) Jessica and Erin of Dabblemade a bold pledge: for the next 30 days, they would chronicle their thoughts in full honesty as they decided what to do with their company, which is on the brink.

Failure? Honesty? These are not things you typically hear when you ask an entrepreneur, “So? How’s it going?” Sharon Schneider from Moxie Jean wrote a post a few months back about a phenomenon she called “the entrepreneur’s hoax,” essentially how saying “We’re crushing it!!!” every time someone asks what’s going on with the company does no good for anyone.

I can emphathize with this hoax very closely: I always feel a little fake and at odds when people ask me what’s going on with matchist. Sure, we’re crushing it. But we’re also facing huge challenges and we need a lot of help and insight to be successful. Lately, I’ve learned that a little bit of honesty among peers goes a long way in promoting healthy dialogue between founders.

By saying we’re always crushing it, we’re hiding and promoting an ugly lie: Entrepreneurship is HARD, it’s harrowing, soul crushing and not in the least bit glamorous. You feel like you’re failing just about 90% of the time, and it’s a real psychological challenge. A great Inc article highlights the psychological price of entrepreneurship, and let’s just saying it’s hefty.

Recently, any time a fellow entrepreneur has asked me the “how’s it going” question, I’ve taken a different approach: “Things are going well, but they can always be better. The challenge for us now is figuring out customer acquisition. What customer acquisition strategies have worked best for you?” As soon as I say this, the veneer of falsehood seems to melt away as people reveal their own best practices and insecurities. I’ve learned SO MUCH just by being honest and asking peers, I’m shocked anyone still pretends everything is peachy keen.

A psychological principle is at play here: the principle of reciprocity. By sharing something and being authentic, humans feel the need to reciprocate. We give when we get. This is the same principle applied to get you to download a free ebook and make a purchase on a SaaS site.

I look forward to reading about Erin and Jessica’s decision making during this tough month, and I applaud them for their integrity and authenticity in sharing such a harrowing time with the public. If only we could all be a little bit more honest, we could help each other and solve our own problems much more quickly.

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Honored to Be Part of Crain’s Chicago Business “20 in Their 20s”

Posted by on May 6, 2013 in Uncategorized | 0 comments

On May 1st, I was chosen to be one of Crain’s Business Chicago “20 in Their 20s.” It was a fun process, sharing my achievements over the past few years, as well as talking about the motivating factors in my life. Below are the two articles about my experience they included:

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Ode to 25

Posted by on Jan 23, 2013 in Uncategorized | 0 comments

Screen Shot 2013-01-22 at 10.37.07 AM


Ever since I was a little girl, I was obsessed with the number 5. Why? I’m not sure. It kept popping up all over the place. When I was 5, it was the best year yet in my life, I remember thinking. I was always 5th in line, channel 5 was my favorite, the number just kept having real significance.

Last year on Jan 22nd, I turned 25. That’s five squared! Not only that, but if you take 1/22 and add together 1+2+2=5. Not to mention it was 2012=2+0+1+2=5. I remember waking up with excitement and thinking: this is my year!

Today I turned a lousy 26. Who even cares? When I think back over the last year, it really was the most magical, important, amazing year in both my professional and personal life.

This time last year I was working on FeeFighters, my first startup. We had recently launched Samurai, our new online payment product. The team was hustling to raise money, built out the product, and move into our first awesome office space. Then something crazy happened: an acquisition offer. Groupon wanted to buy us! (This is back in Groupon’s hey day, on Jan 22nd last year their stock price was over $20, now it’s $4). I felt a range of mixed emotions: Excitement! Disappointment (I loved FeeFighters). Nervousness (would we take it?).

As the negotiations went on, I began to have existential angst. What would I do next if FeeFighters was acquired? I had poured my heart and soul into this startup, joining Sean and Josh fresh out of undergrad and learning so much during our growth trajectory. And would I work at Groupon if they did acquire us? One thing was for certain, I felt in my heart that I was meant to do startups.

We had our officewarming party, knowing that the acquisition was soon to be finalized. We sang karaoke, ate pizza, and talked to our friends and supporters about the exciting year ahead. Soon, the news was out.

And I was left to figure out: What’s next? I signed up for Code Academy (now Starter League) and decided to learn how to code. I scrambled to apply to business school. And then, I thought, which company will I start next?

Code Academy was great: I dove into code for a solid 9 weeks, attending class and coding long days. It helped me evade the existential angst of not knowing what to do. After my bschool application was in, I started to talk to fellow entrepreneurs who had MBAs. Was it worth it? I asked them. For the most part, most people said no. However, when I looked around at the entrepreneurs who I really admired, most of them did have an MBA. Many said it was a hedge in case the startup thing didn’t work out. Some said it was a checkmark on the life list of things to do. And a couple said it really added value for them intellectually.

At 25, an MBA from a top business school seemed like a smart idea. I was hungry for business knowledge and the depth of analysis that my coworkers with MBAs had. However, I have a fundamental ideology in life: personal life always comes first. While Stanford and Harvard seemed like the top schools where I could make new inroads and be at the forefront of startup MBA education, I knew I would not be applying there. My partner, Serge, and I had built a great life together. We supported each other through think and thin, and I could not imagine leaving him, even for two years, to pursue an MBA. While schools in Chicago were on par with other top business schools,  I didn’t want to go to Kellogg (I went to Northwestern undergrad) and the prospect of Booth scared me: I’m not naturally a numbers person.

One of my other life ideologies is this: do things you’re scared to do. So I told myself, either Booth, or no MBA. In May, I found out that I would be attending Booth next fall. I was excited: finally! Karma was definitely on my side when I learned I was the recipient of the Herman Family Fellowship, a scholarship awarded to one female entrepreneur in each class.

Around the time of the acquisition, Tim (my business partner) and I had a serious conversation about the future. We love Entrepreneurs Unpluggd, but we wanted to start another company, something focused on software or SAAS. While we would continue to grow the EU brand, we began to brainstorm ideas for the Next Big Thing.

About a month later we decided to work on matchist, a site for connecting entrepreneurs/startups to developers. Throughout our time at EU, people kept emailing us, asking for recommendations for developers and we couldn’t send them anywhere. Our new company, matchist, would be the solution. Tim started coding in May, and I started interviewing hundreds of entrepreneurs and developers for customer development.

The summer flew by. I worked on matchist, and helped companies at Excelerate Labs. I traveled to London, Italy and Israel at the end of the summer. School started and I dove in, somewhat precariously. Fairly quickly I realized that school would have to take a back seat as matchist became more of a reality and launched in October at Technori Pitch (you can see us here).

If you’re still reading, you must think that this was one hell of a year. But wait! In November, Serge whisked me away from the stress and activities of life for a weekend getaway. We walked around beautiful Lake Geneva with earmuffs, gloves and pink cheeks, admiring the natural beauty. Then, my heart stopped. Serge got down on one knee and proposed.

What followed was a whirlwind of tears, celebration, and planning. The last two months have been a matter of hustling, studying, and wedding planning.

So I greet 26 with a happy smile: I’m ready to be that much closer to 30 with my feet firmly on the ground. What I learned this year was that if you stick to your principles, work hard, and help other people along the way: life won’t do you wrong.

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