Bootstrapping Your Startup

When I first began talking about my startup, I didn’t think that bootstrapping was the answer. I had always been used to making a salary, getting my health insurance covered, having an office, basically buying anything I wanted whenever I wanted because I worked hard for it and deserved it. Well, once I made the leap from full time employment into a full time startup, things dramatically changed. I couldn’t spend time supplementing income because I had to give my undivided attention to my new project. With that, came a lot of stress and financial budgeting.

In a world of sixteen-hour days on your laptop fixing bugs and setting meetings, it’s nice to earn a little extra cash without putting too much of your time into doing so. Here are some of the best ways to make money while you’re building your startup.


1. Become a Zirtual Assistant.

Zirtual is a company based out of San Francisco that provides personal and executive assistance to busy people. If you become a zirtual assistant, you can set your own hours and choose only which jobs fit your schedule.

2. Fulfill requests on Zaarly.

Zaarly allows people to post what they will pay for a task or an item. Sometimes it’s as simple as a ride to the airport for $50. Other times, people are asking for help moving for $500 or a full day wedding photographer for $1,500. Sift through the requests to see which tasks your are able to fulfill.

3. Board a dog. Become a Rover sitter.

Rover was created at Startup Weekend and is a community for dog lovers to connect owners with sitters for home dog stays. So if you love dogs and work from home, you can apply to be a dog sitter in your area.

4. Rent a room out of your house or condo on Airbnb.

If you have a spare room in your place or will be away on vacation for a period of time, consider listing your space on Airbnb.

5. Become a TaskRabbit.

TaskRabbit is similar to Zaarly and Zirtual. People post errands and chores that they want to have done, like buying groceries or moving/packing and the average cost they would pay to have that task accomplished and then certified TaskRabbits will come over and fulfill those requests.

6. Teach a class on Dabble.

Dabble lets you learn, teach and host a one-time affordable class. You can teach what you know and love to a group full of interested students.

7. Become a Ninja or get paid giving advice on Clarity.

LiveNinja is a way to talk with live highly skilled experts via video chat. Clarity is similar but allows business experts to give valuable advice over the phone.

8. Freelance your skills on FreelanceSwitch.

Take a look through the job board on FreelanceSwitch to see if there are any jobs that you could help with. Sometimes it’s a quick blog post that needs written while other times, companies are looking for a freelancer on a major project.

1. Be smart about accounting.

Keeping your financial records maintained from the very start will ensure that you are on track when you start making money. Also make sure that you have a good accountant/CPA to handle your taxes. One of the best ways to reduce costs and expenses in the beginning is by being on top of your taxes and maintaining control. Upsourced Accounting is a firm in Columbus geared specifically to the freelance/startup group.

2. Understaff and consider interns.

There are many students looking for a job in a startup and you might just be the best resource for them to learn and grow.

3. Keep overhead low and outsource.

In the beginning, it is very important to keep the overhead low. You don’t need office space; work from home or coffee shops. When you’re thinking about hiring, first consider outsourcing and then check sites like Elance or oDesk for qualified candidates to do the project virtually.  If you have any quick jobs or surveys to test, give Fivver a try.

4. Negotiate.

Don’t underestimate the power of negotiation. Try asking for discounts on products if you feel that you may not use all of the features. Or perhaps explain that you are just a startup and unable to make those larger payments but will work out an arrangement to refer more clients.

5. Use free web tools.

There are many free tools out there to help you start a company. Take advantage of them. I highlight a few of them in this post: Startup Tools and Must Haves. 

Happy bootstrapping!

Make Life More Valuable: Part II

My first post, Make Life More Valuable: Part I was such a hit that I decided to make it a quarterly feature.


Last summer when I was in Seattle, I decided on a whim, to climb Mount Si and ever since, I can’t stop thinking about the feeling I had when summiting the mountain. When everything was different. When I reached the peak and felt rocks crumbling down below my feet as I climbed higher and higher through the haystack. When I watched the clouds circle the mountain and was left with a view of the world five-thousand feet below me. That moment when I remembered what I was climbing for. Without challenge, life would feel like every other day on the ground.


Have you ever been upset in a moment or stuck on a problem that you just can’t seem to find a way to look at it on the outside, no matter what you do? You keep digging yourself deeper and deeper into the situation in your mind that you have now let this one little worry control your entire world. Well, the only way to really gain control of your emotions is to change the pattern. When you get upset, if you always go to the same place, listen to the same music, think the same thoughts, just stop! Get up, go for a run, act goofy, shake it off, (seriously). No one is watching but you. Get yourself out of the funk and change the pattern. I’m telling you, it’ll help you snap back into reality and let you see the problem from another point of view to find a meaningful solution.


I love this tweet I saw last week “Stop the Glorification of Busy”. The thing is, we can all be busy… drowning in work… so overwhelmed with things to do… etc. But by working SMARTER you can accomplish much more on that to-do list. You just need to be disciplined and set realistic goals. Being an entrepreneur definitely isn’t for everyone. Some people need structure set by someone else. And that’s fine. But if you are willing to make the jump, be sure you know how to manage your time efficiently to get the most out of your work days. Working hard isn’t hard enough if you aren’t working smart.


We spend so much time working to become “successful” “wealthy” or “rich”. We spend even more time trying to figure out what those terms mean to us and how to get there. But what about all of the time in-between? Just be. Enjoy the simple pleasures of life and just simply be. A cup of hot coffee on a rainy day, a walk around the park with my happy Golden, a phone call with my dad for no reason… these are the type of simple pleasures that makes my life more valuable.


The key to a rich life is to invest in yourself. By eating well, sleeping well and exercising often you will be much more productive with work and have a stronger sense of balance. Another important step to investing in yourself is to continue learning and building your knowledge base. I consume tons of information every day by reading books, articles and blog posts or listening to podcasts and TED talks from powerful thought leaders. I find that spending my time and money on growing my personal skills will always be beneficial.


We get so caught up in working out and being hard on ourselves that we deserve to indulgence every now and again. My secret indulgence is Jeni’s Splendid Ice Creams on a hot summer night. Who am I kidding? Jeni’s at any time is delicious.  I even had a little yesterday! [double-toasted coconut + banana cajeta…mmmm].

What are some of your personal tips or tricks on how to make life more valuable?

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!