Category Archives: startup

Answering The Anvil – startup questions from Purdue entrepreneurs

The_Boiler___The_AnvilI went to Purdue and studied mechanical engineering.  It was an amazing education and prepared me in many ways for the work I do now as a software entrepreneur. (technology, software development, critical thinking, data>>opinion, math…).

Recently, I was contacted by a student looking for an internship.  A few emails and an “audition” later, we hired Spencer Brown for the summer.  I applaud his networking (reached out to me directly on LinkedIn), willingness to work at a startup who might/might not be able to hire him back (risky internship) and openness to work through our process or lack of one.  We were specifically impressed with his hacking/building things and proven entrepreneurial interest vs. just school work. We @rivaliq are looking forward to seeing him this summer and building cool stuff for our customers!

Then I was contacted by Grant Gumina, the managing director of, a co-working space at Purdue. He asked me to help out some of the teams who were going through (accelerator) and I happily agreed.  Prior to the talk, I asked him for some frequently asked questions, and while I answered them during a recent Skype call, I wanted to share for the benefit of others.  Here goes;

What’s a recurring mistake have you made that took you a while to figure out?

Doing customer development AFTER I made a product vs. before.  Now, I spend lots of time, focused talking to potential customers using only a hypothesis on what solution I might build to frame the conversation. It’s about asking questions vs. telling them what I made (marketing) and why they need it (sales).  I want to understand as much as I can (problems, existing solutions, buying behavior, influencers, pricing options, keywords…) about a customer segment, as early as I can, and this informs many downstream decisions.

Not understanding the funding sources early in the process.  Talking to investors early, is a useful part of understanding a market as well as when/if I can raise money for a specific idea and the metrics/progress I might need to achieve to get the best investors.  Here is how I think about it now;

Not understanding similar or competitive solutions, again, early in the formation of the idea.  It’s hard to change user behavior so understanding the best solutions in the market today and how ours could be 10X better (enough to dramatically change behavior) is important.  I now do this as soon as I start working on a new idea, often using tools like Rival IQ to understand the existing companies, then triangulating with discussions with customers and investors to get a full picture of the landscape.

What would you do if you were in college again?

I was at Purdue for 5 years, 4 of which I was swimming full-time (on scholarship) as well as being a mechanical engineering student, so I was pretty busy. For my 5th year, I won a scholarship (Red Mackey Award) and was able to spend more time really digging-in and learning vs. just getting by.  For engineers and other technical majors, I’m sure you are equally busy so there is not much time to do “more”.  But, I wish I had spent more time with people who were out in the world doing what I thought I wanted to do.  This could have taken the form of projects or internships but more importantly, trying to understand what people DO on a day to day basis via coffee/short conversations.  In retrospect and looking at my career path, this would have been much more time pure entrepreneurs vs. more corporate roles.

Secondly, I was a proficient programmer, but I would have have spent more actually get “good” in a way that I could have landed a job in that area as well as mechanical engineering.

Finally, more time with designers.  This could have been in graphic design, product design… with a focus on understanding how they think, their processes, how they make decisions….

If your question was about my major, I think ME was a really good foundation.

How do you start to charge users if you’re already giving them the product for free?

This is always a tricky thing, but I would think about it in a few ways.

One, just start charging and let the chips fall where they may.  End users should understand that you need to make money too and that they’ve received your “value” for free.  Be honest with your users and just communicate openly.  The best ones will want to pay you so you keep bringing them value vs. quitting to go work on something else.

Another idea is to pick a set of features which are highly requested, from your best targets (not all users are created equal) and then only charge for these new features leaving the base product alone and remaining free (lead gen).

Another angle is volume based, which means you get to X of something for free and if you want more of X, you need to pay.  See Full Contact Card Reader as an example.

What’s the best way to engage beta testers/early adopters throughout the development process?

I have a longer blog post about this here, but the simple answer is;

  • know who you want and overly focus on a smaller set of highly engaged users.  These will be people who “really, really” want their problem solved and ones who are “experi-mental” meaning they are used to using products early in their lifespan and when they usually suck.

  • blend online means of interacting (email, chat, twitter…) with physical interactions (have real people come to your space and use your product)

  • Build in customer development and feedback into your sprint/development process so you are always meeting new potential users (at least 2-3/week)

  • Give public credit to people who give you ideas, e.g.  “thanks to GrantG for the idea for X” – Put this in release notes, blog posts, tweets…

  • As you get a basis working product, consider some “community” support solutions like or or even a hacky google doc where users can report bugs, suggest features…

  • Focus on “customer success” vs. sales – this means knowing about lots of other solutions in a space, that solve problems for your users in your narrow domain (e.g. Syncing your contacts ( or understanding your competitors ( as well as the broader domain (business productivity) or (digital marketing).  Share suggestions, posts, ideas, solutions widely.  Be a useful resource, even when your product is not the right fit.

  • Suggest content and connections – “you should really read X, follow Y or try Z and if the user is valuable or influential, make connections.

What things have you really wasted time on early in the company’s life?

Focusing too much time trying to convince users that they had the problem I was trying to solve vs. focusing my effort on solving for the people who self- identified and were really wanting a solution.

What strategies or tools do you use to stay productive?

At work, I am a major user of software tools and utilities.  Much more detail and specific tools are here –

I am also still very active and try to exercise for at least 60 minutes/day, usually longer.  I also make sure to get at least 8 hours of sleep on one or more nights each weekend.  Usually only sleep 6-7 during the week. I also eat largely vegetarian (sometimes fish, but no meat) and have done for over 25 years.  Spend at least a few hours each week helping other people, giving advice, sharing what you know…mentor others even when you think you might not have that much to offer.  Just “help-share”.

If anyone else wants to support the cool work they are doing at Purdue, connect and share;

Perfecting your startup pitch

Over the past month I have had the privilege of attending or speaking at a StartupWeekend in Boise, TechStars “for a day” in Seattle, TechStars New York,  Microsoft Kinect Accelerator in Seattle, TechStars Boulder (with Jason Mendelson) and finally mentoring at a Startup Weekend in Medellin, Columbia.  It’s been great to meet so many new and aspiring entrepreneurs in so many cities.  In the process, I’ve heard lots of pitches and coached many on how to make their presentations better.  Here are a few tips;

1.  Find the emotional hook (pain is better than opportunity) – most great companies solve a painful problem and as an entrepreneur you should be able to characterize the user/pain in a way that the audience connects with.  People should hear the pitch and say, “damn, that is a massive pain and I hope they can solve it” and the more they feel it the better.   Bonus points if the pain has some social benefit or very direct and quantified monetary cost.

2.  Compelling data points – For a good pitch you need to have 3-5 strong data points that make the audience think, “wow, that is a big space”.  This is usually the number of users who will be affected, the “cost” of not having the solution and a few examples of similar companies who have been successful solving a similar problem.  Pick the data points and weave them into the story vs. showing complicated graphs and forcing the audience to guess the meaningful numbers. For example, the winning team at SUW Medellin focused on the thousands (they had the real number) of women in Medellin who reported being the victims of violent crime last year and provided them a quick way (the red button on their phone) to report their position to police via sms and Twitter.

3. Show the solution – screen shots, live demos or video of the product are way more compelling than a verbal description of the solution.  Show vs. tell.  Worst case, make realistic screen caps and/or real wireframes of the product, but make it visual as if it really exists.  The closer to working product you can get the better!  Keep the demo to ~30-45 seconds and/or have an animated screen-cap version that you can narrate.

4. Develop your “it’s like” metaphor – Everyone is busy and inundated with ideas, companies, products…so you need a simple hook that they can remember.  Often this can be done with a “it’s like” which combines something they know with something new.  Or, it could be a combination of 2 well known things.  One of the compellig teams in Columbia developed a product that they described as “instagram meets graffiti” – without even seeing the solution, you could imagine what it does, why it would be cool, who might use it and even guess on a freemium business model where you could have virtual spray cans, fonts or other treatments.  Check it out at

5. Stick with one business model (and advertising is not usually very compelling) – I have seen countless teams pitch their idea with several business models (advertising + sponsorships + premium content + paid features…).  Each of these models requires different things from the user and likely different feature prioritization in the product.  Pick one and make a clear case on why it will work. If possible use other comparable companies in your space to validate that this model can work.  For example, with Gist we focused on business professionals and planned to charge a monthly subscription fee.  We based on model on the same users (sales guys) who already paid for solutions like and Blackberry that delivered them an information advantage.  While we could have had targeted ads (like LinkedIn) or API licensing deals (like Full Contact) we wanted to stay very focused on one model.   If you need help developing this, check out this post.

6  KISS – most good ideas are simple or at least sound simple of the surface.  Under the covers, it is likely that there are lots of problems (small and large) that need to be solved, but if it seems simple, people can remember the solution and often they believe the solution can exist quickly vs. it being too complex, complicated and therefore hard to implement, communicate and get right with too many variables.   Keep it simple, stupid.

7.  Passion – You, as the entrepreneur, need to show your passion for the company, the problem, the users, the solution, the team…People want to connect with others who have passion and commitment.  Passion will take you through the tough times, get your teams to work harder and keep your customers engaged when your product is less than ideal.  Get excited, get loud and be passionate when you talk about what you are doing and how it is going to change the lives of your users (and potentially the world)

If you can keep these points in mind, your idea will come across as much more compelling for investors, your team and most important, users who have the problem!

photo credit

NWEN presentation – 0-25mph for startups

Early this morning, I presented at the Northwest Entrepreneur Network breakfast . NWEN ( helps people start companies by giving them tools, connecting them with service providers and making connections to other people, advisors… and I love that. This was a chance for me to summarize my thoughts and experiences (to date) and connect with other entrepreneurs. I always learn something when I do these kinds of events, both about what I have done right/wrong in the past and how I can be better in the future.

Here is a link to the PPT that I presented, a continual work in progress.

I also met a bunch of really interesting people working on cool ideas. Thanks to Jared and Peter for setting up the event and to everyone who asked me such good questions after the talk. I look forward to the future discussions and coffee meetings.

If you have questions or follow-ups you can connect with me on LinkedIn, Twitter, Facebook or send plain old email ( and I will do what I can to help.