Author Archives: Bob Crimmins

About Bob Crimmins

Chronic Technology Entrepreneur, Investor, Philosophy Grad, Poker Instigator, Dad

13 Tips for Getting Help for Your Startup

[This article was originally published on Xconomy, March 24, 2011]

It takes a village to raise a startup. TechStars, and other mentor-driven accelerators, understand this. Experienced entrepreneurs understand this. Investors understand this. New entrepreneurs often do not understand this; and those new entrepreneurs that do understand it often don’t know who they need in their village or how to work with them once they figure it out.

The composition of a startup’s village will depend on the individual needs and personality of the startup, but a common thread will be a network of formal and informal advisors—business advisors, technical advisors, legal advisors, personal advisors. If you’re Andy Sack, Rich Barton, Dan Shapiro or Dave Schappell, then you are an easy phone call (probably speed dial) away from a beer with the top minds in startup ecosystem. If you’re new to the tech startup world, then you need to get busy building your network with folks who can help you. Whether you’ve already found someone willing to spend time with you or are still looking, here are some tips for making the most of their help. As both an advisor and an advisee, I hope to learn something new from your comments as well.

1) Know why a particular advisor is a good fit for you. Early on, it’s tempting to want to talk to any potential advisors who will listen. Resist that urge. Have an understanding of why, specifically, you think it’s valuable to talk to this person. What is it in their current for prior experience that makes them a good fit for you. Do they have relevant expertise within your market, with your technology, with your customers, with potential strategic partners. The person you want to talk to should agree with your assessment. Remember, too, that every good advisor won’t be a good advisor for you. It has to be a good fit on both sides and if it’s not, then don’t force it; close the loop and move on.

2) Go after the correct “tier.” This is corollary to number 1), above… and may sound elitist… but get over it. You may think you want an audience with a hotshot in your space but keep in mind a couple of important things. The nearer the stratosphere an advisor is, the less time (and patience) they’ll have for you. And, if you don’t have your ducks in a pretty straight row then your one chance to make an impression may be squandered. Coupled with the effort it will take to get a warm introduction into them and the long wait to get on their calendar (could be two months or more), this is often a losing proposition. And don’t be surprised when your top-tier advisor’s assistant e-mails you the day before your long-awaited meeting to reschedule because “something has come up.” Also, top-tier folks are just not gonna have much time to spend with you, so you’d do well to think of them as connectors to other people and resources. As such, they will likely be cautious about referring entrepreneurs that they hardly know and/or aren’t confident are ready to risk their reputation on. So keep your powder dry. Work your way up. As your startup (and you) progresses you’ll naturally be ready for more and more top-tier help. It’s not a literal hierarchy and it’s not a caste system, but there are circles of trust and circles of influence; as your network expands and you gain the confidence of experienced people, then your circles will expand and will eventually overlap with higher and higher tiers. In the mean time, you may be better served working with folks closer to earth but with more time and energy to spend with you.

3) Be respectful of time. Know what you want to get out of the time an advisor spends with you. Be concise and specific. It’s easy to spend an hour chewing the fat about your new sliced bread machine, but that’s not a good use of their time or your own for that matter. Ask for 30 minutes instead of 60. Pick a coffee shop within short walking distance of your advisor’s home or office, or ask them to choose the meeting place. As the scheduled end of your meeting or phone call approaches, offer them a graceful exit.

4) Don’t be disagreeable. You don’t have to agree with what an advisor has to say about you, your startup, your product, your market, or your strategy but don’t assume that they are wrong and don’t be defensive. Presumably, you reached out to them for their perspective. If you don’t think they’re right, then drill in more to understand their view. In most cases I think you’ll discover that, if they seem not to “get it”, it’s because you weren’t clear in your explanation of what you’re up to.

5) Be totally f#cking honest… about everything. Experienced entrepreneurs and investors (the folks you’re likely seeking advice from) know how hard it is to be successful with a startup, i.e., it’s really, really hard… even when it’s easy it’s hard. “Fake it till you make it” is bullsh*t and if you aren’t candid with an advisor they are probably going to know it and they will be unlikely to continue to invest their time in you if they don’t trust you. Of course, there may be sensitive topics you’re not ready to talk about and that’s fine, but just say so—serious acts of omission are tantamount to deception and will not help you.

6) Don’t ask someone to sign an NDA for the privilege of helping you. Read everything you need to know in Dan Shapiro’s post on Xconomy, “What You Probably Don’t Know About Non Disclosure Agreements.”

7) Don’t pitch an advisor on investing… maybe never, but at least not for a while. Before an advisor would consider an investment, or referring you to someone who might invest, they are going to want to get to know your business, your product, your market, your model… and especially you. It’s gonna take more than an e-mail intro and a coffee meeting to get there… often much more. If you think an advisor is also a good investor, or connector to other investors, then you can trust that they will know that too. It’s fine to make an ask, eventually, once the advisor is meaningfully engaged with you… but don’t rush it. See Nicole Glaros’s chapter “If You Want Money, Ask for Advice” in Brad Feld’s and David Cohen’s Do More Faster.

8) Listen really well. You don’t have to take notes… in fact, if you’re not good at taking notes then it can be a barrier. But be engaged in understanding what your advisor is saying. Strive more to understand what your advisor is saying than trying to get them to understand what you want to say. Ask lots of questions and follow their lead.

9) Go where they want to take you. This picks up from 8) above.  It’s really good to know in advance where you want the conversation to go and if you’re well prepared, then you have a good chance of accomplishing what you set out for. But keep an open mind and let the advisor take you in new directions that you hadn’t thought about. Some really good things can happen when you do this. In fact, getting a specific answer to a specific question is often the least valuable thing you could get from time spent with an advisor. So don’t fret too much if you don’t get a satisfying “you should do X” answer—which you shouldn’t be looking for anyway! If an advisor’s comments and examples seem off base or inapplicable to your specific challenge… maybe they are; if this happens too much, then the advisor may not be as good (or as good for you) as you thought, and you should move on. But don’t miss the opportunity to look for the lesson behind the story. You don’t always know what you don’t know, and sometimes you will find that the lesson is more applicable than you thought.

10) Follow up. This is so easy to neglect but so important if you want to develop a relationship with an advisor. Thank them for their time, their insights, their offer of introductions. Tell them what you thought was particularly valuable to you about your conversation. Tell them if they made you think about something differently. Tell them what you’re going to do next based on what you heard from them. Remember also that these folks are very busy, so make your communications as concise as possible. A brief followup is also a great way to politely remind an advisor of any deliverables they may have committed to. Finally, be patient. It’s not uncommon for busy folk to take one, two, three weeks to get back to you. You up your chances of a timely response if your communications are brief and specific.

11) Talk to lots of customers before seeking lots of advisors. There are lots of really good reasons to talk to customers early and often. Doing so will also make your time with advisors much more productive… because you’ll understand your own answers to all those pesky market fit/customer development/business model questions that your advisors will have on their minds. Your advisors will appreciate this and it will give them more confidence that you know what you’re doing… which may even get you some additional introductions that s/he would otherwise have held back on until they were confident that you were ready for an important introduction.

12) Develop your network. The more quality, relevant folks who get to know you the easier it will be to find connections to quality, relevant advisors. Go to events, meetings, conferences, parties, wherever you peers congregate. And don’t be the guy who stands around with a beer in your hand waiting for someone to come up and ask you what you do. And don’t hang out the entire night with people you already know! Find clumps of folks you’ve never met, walk up, stick your hand out and introduce yourself. Ask them what they do. Ask all of them. You’ll meet a lot of interesting people this way. Eventually (and remarkably often) you’ll discover someone who is working on something relevant to your project and before you know it you’ll be exchanging business cards and making plans to grab coffee next week. Some of them may even turn out to be valuable advisors.

13) What about a formal board of advisors? There are legalities and logistics to building an advisory board that go beyond the scope I intended for this post. So, while I believe that all the tips above are applicable to both formal and informal advisors, if you’re considering building a formal board of advisors then I suggest you also read Venture Hacks’ posts on advisors.

There you have it… a baker’s dozen worth of lessons I’ve learned over a decade or so of getting help from, and giving help to, startup folks. I hope some of them will help you get more out of your advisor relationships.


Holy Crap!

Has it really been 2 1/2 years since I posted anything here?  Time has really flown by.  I’m feeling “posty” again.


Startups as Poker

For some time I have been struck by the similarities between two of my passions: poker and startups. Some elements they share include patient persistence, mental discipline, controlled aggression, managed risk, subtle strategies, refined intuitions, mental jousting, serious mathematics, personal style and, of course, the thrill of the win.

Some lessons from poker that entrepreneurs would do well to heed:

Bluffing is a tactic, not a strategy. While sometimes you must “fake it before you make it”, you better have something worthwhile to “make” or you’re in for trouble.

Play your game but know your competition… and adapt. There are some tables you just shouldn’t sit down at. Pick your battles and beat your competition where it makes sense to do so.

Be decisive, but not capricious. Decisive doesn’t mean making fast decisions.  There’s a big difference between making timely, thoughtful, justifiably confident decisions and making fast decisions — but don’t take too long either.  Also, understand the limits of the information you have and when don’t have all you wish you had, resort to your experience and intuitions and get on with it.

Know when to hold ’em, know when to fold ’em, when to walk away… and when to run. This is a hard one for a lot of entrepreneurs — giving up is hard to do!   We’ve internalized many of the aphorisms that we hope are true:  “If you follow your passion you’ll be successful”… unless your idea sucks. “Your persistence will pay off”… except when it doesn’t, and sometimes it just won’t.  “Anything is possible if you try hard enough”… except when it’s not possible.  The ability to see past your passion for the possibility of success to the probability is a huge challenge.  This is one area where married entrepreneurs have an advantage — their wives harbor far fewer delusions.


Dragon’s Den — Nowhere in hell….

dragons-denI have always believed there is a special place in hell for the producers of reality TV shows — almost certainly deep within Dante’s 8th Circle. But I must admit I’m now addicted to one, namely Dragon’s Den.

The program originated in Japan in 2001 and has since spread to more than a dozen countries worldwide, with a U.S. based version called “The Shark Tank” trying to get off the ground this year. My favorite is the UK version, now in its 6th season. Each program is a cavalcade of entrepreneurs and inventors looking to fund their life’s dream with money from smart, successful and unforgiving angel investors. However, while it technically is reality TV, it doesn’t suffer from all the BS that so many others do: the contrived living arrangements, the hormone-driven hard bodies, the so-obviously juxta-opposed racial and class backgrounds, and the inevitable infusion of alcohol.. aaarrrrrrrg! Rather, it’s chock full of earnest folks who believe in their ideas but who need to sell the investors through their pitch.

The pitches range from inspired to naive to downright embarrassing — but all are sincere. Relatively speaking, the businesses are not complex and the stakes are small — i.e., typically between 50K and 250K pounds sterling (about $75K – $375K in US dollars). Each of the Dragons is worth in the range of between about $150M to $800M, a respectable fortune by most measures (and certainly worthy of this would be entrepreneur’s respect.) And while the business ideas run the gamut from brilliant to absurd, what is striking is the consistent themes that emerge from the questions posed by the Dragons. Because of the (relatively) low stakes and the occaisional bizzaro pitch, it would be easy to write off the program as an entrepreneurial amateur hour, the Gong Show of angel investing — but that would be a mistake. The themes that emerge are virtually 100% consistent with what I’ve witnessed and learned over the past handful of years of entrepreneurial pursuit. Whether analyzing a market, writing a business plan, developing a product or pitching investors, there are basic lessons that emerge from Dragons Den that transcend the particulars of industry vertical, product category, market size and capital structure. This is not to say that there are not additional complexities and strategies that accompany increases in scale; this is just to say that there are fundamentals that apply startup fund raising across the board. The similarity in the application of these fundamentals is what fascinates me.


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