Entrepreneurship Starts with Asking Someone to Buy


Remember to ask for the sale. You’ve probably heard these words of advice many times – whether in the context of a prospective deal, a request for a favor, or in an interview prep – and the first time you made the ask it was probably really scary. Asking for the sale is the first step to becoming an entrepreneur. When you ask someone to buy what you’re selling, you really know whether they will vote with their wallet and trust you to provide them with value.

My son has been talking about selling the friendship bracelets he makes for months. I heard about many potential business models. There was the “set up a stand at the end of the road” during the summer, the “find people at school to buy it” model, and several other less promising ideas. And the one that won the day today was “Mom? Can you give me your phone to take some pictures? I want to sell my bracelets to people I know and I hope you can post the pictures on Facebook.” The simplest business model sometimes is the best.

When you face a challenge, it’s really easy to say “I’ll think about it tomorrow” or “it’s not quite right yet” or “I don’t have all of the answers.” It’s really important to take the biggest small step you can take to move toward that goal. You won’t get it right, but one step forward is better than no steps at all.

My son is now getting orders for his bracelets, learning how to fill orders, take commissions, and deal with inventory. He is selling these bracelets for a goal – earning enough money to buy a concert-level trumpet – and he’s also learning about the details of small business. (I believe there is some side negotiation with contract labor and his little sister.) What stopped him from doing this before? Inertia. Today he decided to ask for the sale and people are buying.

“I think it’s so cool that you would do this for me,” he told his Mom today, “thank you so much.” Very soon I think he’ll figure out that he did most of this for himself. We enabled him to take the first step toward starting his business – and I hope it won’t be his last one.

Be right when someone asks.

Lemonade Stand
photo by http://www.flickr.com/photos/billynata/5053274054/

This essay is written as part of the Startup Edition project – check out the other essays here.


When was the last time you were right? Absolutely, positively certain with no chance of being wrong. Now, think of the last time you knew you had the answer, and someone asked you to be right? How did that feel?

If there’s one lesson I could share with young entrepreneurs (and with my younger self), it would be that you should only try to be right when someone asks you for that absolutely certain answer. The rest of the time, be nice – wait for your moment until you get asked the question you’ve been anticipating.

Can you gather facts? Sure. Can you prepare persuasive arguments? Absolutely. And until someone’s listening, those facts and arguments don’t matter much.

What does it mean to be right at the wrong time?

Being right doesn’t prove you’re smart – it often proves that you are impatient and can’t wait for the right moment to make your point and back it up with the information the other person or people need to understand. Being right also doesn’t make you right in a given situation (sounds strange, right?)

Compare and contrast the feeling of blurting out the right answer in a crowd that hasn’t asked for it yet against the feeling of being just the right person to answer just the right question at the moment it’s asked. Answering the call for an important question can be an amazing feeling – you get to show how smart you are, you know you’re solving an important problem, and you know someone actually wants to hear the answer.

On the Importance of Timing

Wait, you say. Aren’t some of the most important questions the ones that haven’t yet been asked? Yep. That’s true also. And if you can manage to lead an individual, a group, or an audience to ask you the question that you know how to answer and help them to feel that it’s their question? That’s charisma – the ability to lead and inspire without the implication of being a know-it-all – and it’s a great goal to pursue.

There are other lessons young entrepreneurs need to learn. These are ideas like “do more of what you love,” “hang out with lots of smart people and interesting things will happen,” and “don’t spend too much time at big companies without also talking to people at small companies.” You’ll find lots of these ideas (and the ones that work for you) by continuing to learn and meet new people.

When you meet new people and want them to listen to your ideas, answer the questions they ask. If they haven’t answered the question you wanted to ask yet, guide them to ask it. You’ll be happier when you see the spark in their eyes as you enthusiastically answer the right question.

This essay is written as part of the Startup Edition project – check out the other essays here.

9 Rules for Being an Effective Mentor

"Do, or do not. There is no try."
photo by http://www.flickr.com/photos/xtyler/

In my experience, having effective, talented, and knowledgeable mentors has been the most powerful startup accelerator that I know. The best mentors I’ve worked with do a lot of the things on this list. You can call these the 9 rules of being a mentor – they will help you provide feedback to entrepreneurs you know and respect. These are not meant to be a definitive list (you should make your own list of things that work) and will get you started toward the process of sharing your expertise with a startup team.

Rule #1: Use your Superpower (and know what it is)

Maybe you are amazing at Operations. Perhaps you understand Finance better than anyone you know. Or you can design an email marketing campaign to ensure the highest percentage of opened emails. You know your superpower (or you should) – and you can be a really effective mentor if you can leverage your experience in a way that doesn’t say “do this, or else” to the entrepreneur you’re advising.

Rule #2: Be Mindful of Limited Time

You are busy; the entrepreneurs are busy too. So show up on time, whether it’s an in person meeting or a phone call. Give people information to review before the meeting. And answer any questions promptly so that you can give the best impression possible to a budding entrepreneur about how you can do things the right way. (Bonus points awarded if you thank them for emailing you and demonstrate a great customer service affect.)

Rule #3: Give to Get

This mentoring relationship is not about you: it’s about what you can provide to a person trying to do a very difficult thing. If you do nothing else with your mentoring relationship, you should be focusing on what the other person says that they need (and listening for the unspoken, unmet needs as well.) You can also use the power of your networks to spread the word and really amplify the efforts of a fledgling business.

Rule #4: Make Introductions and Provide Context

I’m sure you’ve received more than a few emails or requests in your time where you read the email and are not sure why the person is contacting you and how they would like you to help. Providing context makes things better for you, the entrepreneurs, and anyone else they are working with. For example, “This is ____, he/she is solving this problem ____ for this customer ___ . It would be great if you could (clearly defined ask) by (clearly defined date.) If this doesn’t work for you, please suggest another resource who might be able to help.” is a short, focused way to request assistance. You may also need to do a “pre-ask” and make sure the resource is willing and able to help.

Rule #5: Build a Community of Mentors

A community is only as effective as its members, and the totality of the network provides the relationships and ideas that make the network really thrive and grow in value. Please meet the other Mentors, the other startups, and be open to the idea that you are always learning. You never know what a day will bring when you’re open to new opportunities.

Rule #6: Only Offer What You can Deliver

The relationship with your startup company will be better if you set ground rules for how you can be contacted, what you can offer, and what you’re expecting to give. (You might ask the same questions of them.) Setting these expectations up front will avoid disappointment and will make it clear what sort of communication cadence you need to build.

Rule #7: Make “Checking In” into a Habit

Set up a regular meeting with your team – either in person or on Skype – and encourage the entrepreneurs to drive the meeting using a well-defined agenda. A great start to an agenda (use your own best one) is “what I did, what I’m doing, and where I need help.” Sending answers to the same set of questions is also a great way for teams to inform their mentors – a tool like iDoneThis or 15Five or a shared Google Doc can do the trick here.

Rule #8: It’s Not Your Startup

Building a relationship with a set of entrepreneurs is exciting, and sometimes develops into a lifelong relationship. And remember that you are there to provide advice, to help frame decisions, and to be correct when someone asks you a specific question. But it’s not your startup. Remembering that fact makes it easier for you to deliver difficult and important advice, and it also frees the entrepreneurs to ignore your advice when they need to make their own way.

Rule #9: Ask the Right Questions

In best Steve Blank form, encourage your teams to “Get Out of the Building” and validate their assumptions with real customers as soon as possible. You can help them build their hypotheses by asking incisive questions, but ensure they make key decisions based on the customer insights they uncover during customer validation.

Are these the same rules I would have written when I first joined a startup? Nope. So remind yourself that your own personal rules for serving as a mentor (and for being mentored) will change over time. Your job as a mentor should be to focus on creating, communicating, and delivering unique value for the startup you’re mentoring, and to help them do the same for their customers.

The circle of startup life

Photo by http://www.flickr.com/photos/kevenlaw/

It’s a sad day in a way – today marks the end of Gist, a company I had the pleasure of working for through its evolution from a scrappy startup pioneering new ways to manage social contacts through its acquisition by Research in Motion – the BlackBerry folks. And it’s a happy (albeit bittersweet) day as well. The end of Gist is a great time to reflect on the nature and purpose of startups – how fickle they are, how fragile, and how magical.

I love startups because they strip away the unnecessary parts of corporate america and focus on putting together a team to address a market and (hopefully) to solve a problem that people (and customers) want solved. Asking customers to hire your startup for the job they want solved – and hearing feedback from them that you solved that job well – is a great rush.

The purpose of a startup is – I think – very simple. The goal is to either build a grand, successful business, attract acquisition potential (and culminate in an acquisition), or to fail – as quickly as possible. That sounds a bit harsh when you put it that way but consider it as an efficient use of capital to make more capital. Along the way there are great relationships built, features created, and features (and products thrown away or pivoted because … sometimes … customers don’t think the way that you do.)

Working in a startup can be quite tiring (even if it’s also amazing.) It’s hard because the impetus to get things done is almost certainly self-driven. Customers will ask you to build features and functionality, and the team is the only driver to actually make that happen. There are always constraints, be they money, time, or people. And the reward for working in that startup is most often the reward of a challenge met, a job (sometimes well) done, and the knowledge that “hey, we did that.” is quite cool.

And surviving and thriving in a startup (or in a small, entreprenuerial business unit after that startup has been successfully acquired) is an ongoing process. There are some days when it’s hard to listen to customers ask you about a feature that’s not done yet; or when you’re not sure what to do next; or when you’d just like more sleep. And there are more days when you look at what’s possible to get done in a brief amount of time with small amounts of resources and the result is nothing short of amazing.

Creative Process #1: Why Whiteboard?

What’s your creative process? Reading Tyler Cowen‘s “Create Your Own Economy” and Temple Grandin‘s “Thinking in Pictures” has inspired me to look at my own creative process and to examine the ways in which I do and don’t think like my peers. Let me start by stating that I think that a diversity of views is essential and that I don’t have the monopoly (or even the best) method of creating — but it is my own — and that I’m going to use blogging as a method of exploring that process.

One of the best ways that I create is on a dry-erase whiteboard. Whether the whiteboard is small or the size of a wall, there’s something about the surface that challenges me to think big, to fail quickly and fast, and to collaborate easily with others. In short: whiteboards give me all of the qualities of a successful entrepreneur or project leader. So what it is it about whiteboards that makes this process possible?

Why Whiteboard, Reason #1: Think in Real Time

Why Whiteboard #1
The first reason I whiteboard is that it encourages real-time thinking. How many times have you started an idea, a blog post, or a project, only to find that when it came out of your head it was really only half done (half-baked, sometimes)? Whiteboarding gives you a safe space to work those ideas out as they are happening, to add from here and subtract from there, and to say the idea out loud. Sometimes it gives it more weight; other times, just helps you to realize the idea wasn’t that great after all.

Why Whiteboard, Reason #2: Pictures > Words

Why Whiteboard #2
This one’s probably obvious, but pictures are much stronger carriers of emotion than words. The old saw not withstanding, a picture is worth at least 500 words if not 1000. If you can’t think about what you’re trying to say in pictures (and you’re a visual thinker like me) then you’re in trouble. For me, drawing a picture helps me to think about the problem in a different way and to abstract more complicated ideas in terms that are easier to explain. It also helps me/cues me to be consistent about the terms I’m using so that I don’t distract the reader/viewer with new ways to say/explain the same thing.

Why Whiteboard, Reason #3: Make Mistakes. Try Again.

why whiteboard? #3
Reason 3 is a pretty obvious corollary to Reason 1, but is different. Reason 1, Real-time thinking, implies that you’re going to keep working on a problem and solve it in the moment. Reason 3 is to remind you that some times you can just throw out your mistakes, erase the board, and start over.

So there’s the blueprint for my creative process. Think in real time. Pictures > Words. Make mistakes and try again. This actually maps well to other forms of making content, including writing, speaking, and collaborating. The better able you are to suggest the smallest big idea you know how to do, start working on implementing that idea, and then throwing out when it’s clear that you’ve measured it and it doesn’t work, the better you’ll be able to germinate and build new ideas, sparking your creative process. Give it a try! I’d love to see your whiteboard drawings.

Blog at WordPress.com.

Up ↑

%d bloggers like this: