Comfortable with Uncertainty

Getting Comfortable with Uncertainty

It was five months ago exactly when I showed up in Chicago for my first real business meeting about my new startup idea. The weekend prior was rainy, so naturally, I spent 28 hours creating my initial business plan and pitch deck in my own little startup-weekend bedroom. I felt prepared, excited and nervous as I presented to a friend of a friend in hopes of getting honest feedback and gaining valuable connections.

As soon as I was finished, he gave me his thoughts and I couldn’t have been more appreciative and willing to listen. “This timeline is incredibly optimistic. You should consider another logo. A board of advisors would be a good idea. You need to bootstrap your costs. Investors what to see a credible team.”

But the thing that really hit home was when he said that he had interviewed hundreds of startup founders and the one thing that all of the successful founders had in common was their comfort level with ambiguity. As he analyzed my perfectly prepared binder with labeled tabs and spreadsheets of optimistic sales, he asked how I felt about ambiguity. At the time, I wasn’t really sure. All of my decisions up until that point, were made because I wanted them that way, not because something hadn’t worked out as planned.

As time has gone by, I’ve discovered that I will never be completely prepared for this lifestyle. I will never know exactly what to do or have the answers to every question. Each person I meet with will always give mixed advice and opinions that I have to take with a grain of salt and ultimately make the right (and sometimes wrong) decisions in an effort to keep pushing forward. I will always have to carve out a percentage of my day to learn, read, listen and grow.

But now, at least I know that my level of comfort with uncertainty is much higher than when I started. I jumped. Three short months ago. I jumped with complete passion and ambition to make this idea a reality.

This roller coaster is just getting started but it’s all about that moment at the top when you can see above everything else, feel the cool breeze on your face with a knot in your stomach and excitement for the next wave of momentum to keep you going.

Let’s Take Notes

Blogs and books from experienced entrepreneurs are really the best way to start learning. So, if you have the desire to pursue a startup idea but don’t know where to begin, here are a few resources to help.

  • Both Sides of the Table – Startup Advice – Mark Suster is a two time entrepreneur that turned VC. He blogs about being both the entrepreneur and the VC and provides very valuable information.
  • Venture Hacks – Although it hasn’t had much progress lately, this blog is full of amazing advice from seasoned founders and investors.
  • On Startups – This blog provides insightful information for entrepreneurs from “14 Ways to be a Great Startup CEO” to “How to Get Media Coverage for Your Startup”
  • Technori – Based out of Chicago, this blog features interviews with startup founders as well as advice and tips relating to technology, business and entrepreneurship in general.
  • Steve Blank Startup Tools – This is an absolute list of every resource for you to use at any stage of your startup journey. Seriously, this could take you months to get through but it would be well worth the time.

And lastly, I’ve provided a few prior blog posts with great value:

As always, keep moving forward but don’t forget to enjoy the ride. 

Business Lessons Learned in 2012

business lessons learned in 2012

I was reading a Fast Company series this morning in which they asked several innovative thought leaders what each had learned in 2012 and what lessons will carry through to the new year. I’m a sucker for business wisdom from those that have been there and succeeded, so I really appreciated the advice.

Although I’m at a stage right now where I’m also looking for mentors and guidance, I’ve noticed that since I started on my own full-time, I’ve gotten several questions from friends about what I’m up to and how I’m doing what I’m doing.

So here are a few of my own lessons learned in 2012 – from an entrepreneur who is pushing through meeting by meeting and learning every single day.

100% of nothing is still nothing. When starting a business where you are seeking investment and co-founders, you have to consider the obvious: dilution and giving up equity is inevitable. You just have to learn how to slice the pie. Of course there isn’t a right or wrong answer but there are a few tools to help you figure it out.

  • Slicing the Pie – This is a great resource to help you determine how equity should be split in an early stage startup. You can even download the Excel sheet to calculate the values here.
  • – A co-founder equity calculator that is easy to use and understand.

Weeble wobble but don’t fall down. In an early stage startup you have to be flexible with almost everything because, like it or not, you will pivot. For me, it was the name and branding of the company. I had it in my mind that the name and branding would be something that I had come up with way back when I started thinking about the company. I tried everything to keep it that way but after meetings with my co-founder and months of not loving logo drafts, we decided to change the name entirely and create a whole new brand. Although I was sad to see my original idea disappear, I am thrilled that we made the switch and even happier that it was so early on. Here are a few sites I used to figure out how to name our startup.

Advice is invaluable. It is so important to network and connect with as many people as possible. Seriously, aside from doing A TON of research on your market space and after you have created all of your initial pitch documents (plan, presentation, business model canvas, etc.), make sure to set up multiple meeting with like-minded entrepreneurs, investors, lawyers, accountants, corporate businesspeople, VCs, CEOs, friends, whoever!

I can’t tell you how many people I’ve met with in the past 60 days, but I do know that from each and every meeting I gained a little more knowledge and a lot more inspiration. They opened my eyes to ideas I hadn’t thought of and questions I didn’t have answers to. They shared stories of their experiences, things I can expect, things I should watch out for, people I should know and much more. Here are some of the ways that I used these coffee meetups to help improve my startup’s potential.

  • Research. Before your meeting, find out a little about the person you are meeting with so that you can begin the relationship feeling like you already know one another.
  • Bring material. If you have any of the essential items for starting your business, bring them with you. Everyone wants to see a demo, presentation, business plan or even just sketches of the website. It helps them conceptualize your idea and give you honest feedback on your newborn project.
  • Make notes. After the meeting (and sometimes during) I would write in my networking journal: the date, time and place of the meeting and then included a long list of everything that we discussed: feedback, initial thoughts or reactions to my ideas on the software, people that they mentioned who could help with this journey, advice and any books or quotes that they referenced.
  • Do more research. Once you’ve written all of your notes, start looking up the people, websites, tools and books that the person you met with suggested.
  • Follow up. Send a follow up email thanking your new friend for the time and advice. Tell them what you found most inspiring about the meeting or ask them a few follow up questions. Who knows, maybe you can lend them a hand when they need it down the road.

Look, your idea might be amazing… absolutely unbelievable … world changing, even! But it’s just an idea.

In order to turn your idea into a business, you have to work really hard, suck up a lot of pride, realize what you are not-so-good at, find awesome team members to compliment you, get a ton of advice, and find your customers to make the product or service with you.

This post was inspired by this Fast Company series.

Top 10 Gifts For The Startup Entrepreneur

Many entrepreneurs don’t even know it’s time for the holidays until they hear the chimes of bells and holiday music playing in their local coffee-shop. And although most entrepreneurs would agree that the number one thing they want for Christmas this year is more time in a day, that’s not quite something that you can wrap up and slide under the tree. It’s time to give the startup person in your life something they will actually use.

1) Branding and Logo Design 

An essential piece of the startup pie begins with branding and logo design. If you’re looking for the perfect gift for someone that is just starting a business, talk to a local designer about holiday gift options. Maybe you can purchase a branding consultation or the entire logo design.

2) Liveplan & Business Model Canvas 

These apps are perfect for turning business ideas into actual plans. For $30 (for the business model canvas app) and $20 per month (for Liveplan), your friend will be able to organize his thoughts and set forth on his startup journey.

3) Pack of 5 Top Business Books

4) AquaNotes or Shower Notebook

For those that have all of the greatest ideas in the shower…

5) Sky Wifi Smartpen

Yes! I love this. This smartpen records everything you write AND hear as you’re writing and then wirelessly sends it to your computer. You can also play back the recordings from where you were in your notes by just simply touching the notepad. Perfect for long meetings or seminars.

6) Evernote Smart Notebook

Similar to the Sky pen, this is a notebook by Moleskine (win) that works with Evernote to capture your handwritten notes and make them electronic. This is a much more affordable gift compared to the Sky wifi pen but also serves a great purpose for those, like myself, that love writing in notebooks.

7) Headphones

A nice pair of quality headphones are important for the businessperson that needs to focus on work and block out surrounding noise. Also great for traveling!

8) Field Notes or Moleskine

I can’t get enough beautifully constructed notebooks and with all of the meetings I go to, I make sure to bring one of my Moleskine or Field Notes books to jot down reminders and notes.

9) Business Cards (

Help your favorite entrepreneur make a great first impression with potential clients or investors with new snazzy business cards. I just received a few cards from and was highly impressed with the quality, character and packaging.

10) Coffee Shop Gift Cards

You can never go wrong with a coffee-shop gift card. Without the ability to escape to an (out of home) office, most entrepreneurs consider their local coffee shops as a second home. A gift card to Starbucks or even a pound of beans and a fun mug would be just enough to get your startup friend’s creativity brewing.

Are you an entrepreneur with a wish list this holiday season? I’d love to hear what you’re hoping to unwrap. Leave a comment below!

Make Life More Valuable: Part I

In my life, my most treasured moments either stem from family or exploring. I am so thankful to have the ability to travel the world, explore new places and learn different culture. Even if it’s just a little weekend getaway in a cabin with my girlfriends or a ten day adventure to several European cities, I find that the art of travel brings creativity and inspiration to everyday life.

Last Winter, I took ballroom dancing lessons and never imagined it would bring such value to my life. But not even just ballroom dancing — dancing in any form is a beautiful way to express yourself. Have you ever gotten in the car, turned on your music as loud as possible and danced around in the driver’s seat all alone? Well, I tend to do that more often than I’d admit. There’s just something about losing yourself in moves that makes the worries in the world seem so minuscule.

Sometimes I forget to take a break. I run, run, run and then when I finally catch my breath, I am reminded how amazing it feels. I like to just rest…relax…read a book, drink a cup of tea on my balcony and watch the sunrise. Seriously, take time to relax because when you have a chance to actually see the world spinning, it’s a beautiful thing.

A healthy lifestyle makes for a healthy business and a healthy relationship with yourself and others. Fitness and nutrition have  always been an important part of my nature. My personal recipe for healthy living is: juice (once a day, usually breakfast) + cardio (three times per week) + weight lifting (three times per week) and if you’re good, you can build a routine to put them together alternating days on different muscles. One of the best things I’ve ever done for myself was hiring a personal trainer. I learned what type of weight lifting I should be doing for my body structure and goals.

Something I’ve struggled with for many years is my fear of loneliness. I’ve always been committed to overcoming that by trying to find things I enjoy doing by myself. That led me to moving into my first apartment by myself and really getting used to the feeling of solitude. In that time, I experienced some of my most creative moments. I painted, wrote poetry, read classic novels, watched foreign films and documentaries, shot some of my most compelling images and even learned how to grow a window garden (OK, so maybe I was still a little unsure of the whole living alone thing during that time.) But that point is, I did it.

Something that has added so much more value to my life of late is actually volunteering in order to improve the life of others. This year, I will be choosing one organization each month to donate my time and efforts to help those in need. After covering twelve different volunteer categories, I hope to find the ones that need the most and build a relationship with them and contribute as often as possible. Not only is volunteering a great way to give back to the community but you can also meet amazing individuals and learn a lot about yourself in the process.

These two simple words can change everything.

What is some of the best advice you’ve heard or given about making life more valuable?

Inspire: Podcasts for Entrepreneurs

Podcasts are a great source for knowledge, startup tips and inspiration. I typically listen to podcasts in the morning while drinking my coffee and sifting through emails or even during my mid-day break while running at the gym. Since I don’t always have the time to open a good business book, podcasts give me the ability to learn more about marketing, business, economics, and education. Sometimes, I like to speed the programs up on my iPhone to 1.5x to get through the programs quickly but still retain information. A list of my favorites include:

1) NPR: From Scratch – Host, Jessica Harris interviews some of the most reputable CEOs, Entrepreneurs and Founders of today’s business world.

2) Stanford University’s Entrepreneurship Corner – A treasure chest for startups, this site had over 2000 free videos and podcasts featuring innovative thought leaders and business profiles.

3) Startups for the Rest of Us – This podcast provides an amazing amount of valuable information about the startup life for developers, designers and entrepreneurs that are launching software products.

4) This American Life – Ira Glass hosts this weekly, hour long podcast that features journalistic nonfiction, essays and compelling short stories. I’ve been listening to this station for many years and find myself crying or laughing along with the author.

5) NPR: Planet Money – The Economy, Explained. Planet Money’s team does a incredible job of taking the complexities of global economy and interpreting it for the average American. After listening to a couple episodes of Planet Money, you’ll feel like you’ve known these guys for years.

6) HBR Ideacast – Harvard Business Review podcast features breakthrough ideas and commentary from leading minds in management. A great way to learn something new!

7) TED Radio Hour: Building a Better Classroom – Although this entire podcast has inspiring lectures, I found this episode with Sir Ken Robinson to be most interesting. He discusses education today and how to bring creativity back into the classroom. “If you’re not prepared to be wrong, you’ll never come up with anything original.”

8) The Lifestyle Business Podcast – This podcast provides tips for living a mobile business lifestyle. They also offer an private membership and host worldwide conferences. If you’ve ever thought about business location independence, this is the program for you.

9) Startup Slingshot – Listen to this podcast if you’re a hungry entrepreneur looking for tools, tips and tactics about launching and growing a technology startup.

10) Mixergy – This podcast is a collection of business tips and interviews with well-known proven entrepreneurs. The success stories and passion within them is enough to encourage the startup life for anyone.

and just a few more….

What are your favorite podcasts? Did I miss one that you swear by? Leave a comment!