Category Archives: entrepreneurship

Thru the looking glass: Fund-Raising Lessons

Handling QA in investor pitches

Udemy’s Gagan Biyani wrote a super useful, practical guide on fund-raising lessons learned.  Gagan is a great Silicon Valley startup CEO: he’s tireless, he’s persistent, he’s nice, and he’s adaptive.  All that comes through in his post.  Give it a read here

He set an example that I wanted to follow on slightly with some of my own lessons learned and lessons borrowed.  I’ve gained the opportunity to participate in the fund-raising process from a few angles. As an entrepreneur, I’ve raised money for my own company, Moonshoot.   I’m also at times a venture capitalist/investor at BlueRun Ventures, so I see things from the other side of the table too.  

I’m putting together a series of posts, which aim to share these learnings.  I’m going to start this series with one of the most important –and under-discussed – elements of the fund-raising process: answering questions.  

“Say it once.  Say it well.  Don’t say it again.”

I attribute this quote to one of my best friends, Nils Gilman.  An intellectual historian, published author, and polymath, Nils is a fountain of knowledge, thinking and ideas.  He can also flat out turn out well-written text at a factory pace—it’s crazy.  He uses the above adage, in coaching me on writing.  I apply it to what we say, specifically when answering questions in a pitch. 

Why questions matter

Most fund-raising posts will focus on pitch decks, meeting etiquette, etc.  All that stuff is useful.  In my experience though, a key skill for any founding team is how to answer questions.  Investors want to ask questions to probe more deeply and to see how you respond.   In addition to getting us information we want, asking questions provides a different lens into the thinking and quality of the founding team.  How you answer questions conveys a great deal about you, your team,  your credibility, your command of data, etc.   You may not win by answering questions well; you risk a lot by answering poorly.

Where to Start

As answering question is more improvisational, it tends to get less attention than preparing a pitch, getting the deck in shape, etc..  Don’t ignore questions though—spend time thinking about how you want to answer questions.  Nothing is more painful than presenting a great pitch, only to feel as though you gooned a few key questions and lost your credibility in front of a potential investor. 

I recommend Jerry Weissman’s book, In the Line of Fire: How to Handle Tough Questions.  Jerry is a friend, mentor and teacher.  He’s one of the very best in presentation training and skills.  His thinking and exercises on Q&A (and among presentation planning) are among the best.  Get his book here.

I also recommend writing down the top 10 questions you expect.  Figure out how you want to answer them, and answer them that way.  As you go through pitching, write down the questions you’re getting, along with the answers you provide at the time.  Assess whether there are better answers you could have provided, and add that to your repertoire.  Evolve this so that as you do this more, you’re ready.    

My Observations

Few founding teams handle questions extremely well.  Many struggle with basics—hearing the question asked and answering.  For example, if an investor asks you if you’ve raised previous money, a simple “yes, we’ve raised $80K in friends and family” is a fine answer.  Instead, often there’s some whole discussion of who gave you money, when all it came in, why you took it, etc.   TMI.  Understand the question being asked, and answer it.  Remember the adage:

Say it once.  Say it well.  Don’t say it again.

Focus on this, and you’ll be in good shape. 

As you are focusing on this, I’ll add the two most common breakdowns I see in founders answering questions during a pitch.  Though different, they’re related.  Here are the two most common problems I see in answering questions in a pitch:

Answering about the unknowns

Founders are dealing with big unknowns.  Known unknowns and unknown unknowns.  As someone assessing whether I’d invest, I know you’re dealing with unknowns.  Its generally fine to say, “I don’t know, and here’s my plan to learn/figure out.”  So long as this is credible, that’s fine. 

There are two cases where that does not work.  First, you say you don’t know, when I think you reasonably should.  For example, this summer I spoke to a mobile location-based platform company seeking investment.  The exec with whom I spoke hadn’t heard of FourSquare.  This was unacceptable, as this person should have known of them—something he should have been able to figure out. 

The second is where you dress up the “I don’t know,” in a bunch of bullshit.  I have sympathy for this mistake.  As a founder, we want to know everything on the business.  We don’t want to feel like we don’t know an answer to a question.  We may even have some decent hypotheses.  But if you don’t know, you don’t know.  Just say, “I don’t know yet.  I plan to figure that out this way.”  BS is pretty easy to identify and its hard to watch.  I understand the temptation, but avoid. 

Answering about the knowns. 

If founders talk too much about what they don’t know, they are also prone to talking to much in answering questions on details that they do know.  The problem here is lack of empathy.  Investors are flying at a different altitude than the founder.  Founders have everything invested in a company, and are very close to the businness.  Investors are much more removed—trying to assess in a brief conversation the viability of potentially investing  money in a venture.  An investor is flashing through in his/her mind whether the market, the team, and product could be a fit.  This mismatch leads to times where an investor can feel a pitching founder is just off on a tangent and “in the weeds” to a degree that they won’t be able to manage or lead a company.   

Sometimes an investor really is interested in getting down into the weeds, but that’s pretty rare.  As a founder, you should know whether the investor is asking for that detail—if yes, then go into weeds.  If not, hold back. 

I posit that when most potential investors ask a question, they want to see whether a founder can understand it quickly and credibly clarify the essence of what I’m asking.  Sounds easy; hard to do.  Most of us are so close to our specific worldview that its difficult to context switch and communicate at a more bubbled up level. 

For example, I spoke by phone with the CEO of an outstanding company this summer.  Very clearly, they’d built a better mousetrap.  The issue was, no question I asked, regardless of how basic, had less than an 8 minute answer.  This did damage.  I literally got spooked because the executive’s answers were too disjointed and long.

As I reflect on this, it could well be that these symptoms are related.  As founders, we want to hide the stuff we don’t know and expand the stuff we do.  The result is unsurprising.  For stuff we don’t know, we retreat and hem and haw and deflect.  For the stuff we do, we want to expound and show you in 10 different ways why we know this particular thing.  The problem is, both are exactly the wrong approach.  Which leads me back to the mantra I’m repeating…

Say it once.  Say it well.  Don’t say it again.

In conclusion, I’m kicking off my series on pitching observations with a (hopefully) useful primer on answering questions.  Think about this.  Write down key questions you expect and prepare answers.  Track the questions you get asked and how you answered them.  Be mindful of whether you’re more effective saying “I don’t know, but…” or answering what you do know. 

And good luck.  Happy hunting. 



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Pitch Advice from Jerry Bruckheimer

2010 has been a busy year for me.  We launched Moonshoot in Japan, and that’s going well.  I’ve done a few talks at the Founders Institute, some friends of mine and I built Smackdaddy for the IPhone, and I’ve begun helping out part-time at BlueRun Ventures.  All in all, a busy 3 quarters so far, which has led to a dearth of blogging.

To re-enter the blogosphere, I’m planning on spending several posts sharing learning I’ve had in the fund-raising process–both as an entrepreneur (by day) and as a vc (by night).   This first one is a story I’ve told analogue about 5 times in the past 2 weeks, so I figured I should probably post it to the blog and share it potentially more broadly.  It has to do with a key reality in pitches or startups that you need to think about when you are getting started or pitching.  Namely, is the business one that’s going to emotionally draw someone in?

My inspiration for this emotional connection is uber-producer Jerry Bruckheimer, whom Wikipedia credits with over 40 feature film productions.  His movies rock, I love them.  Years ago, I recall reading an interview of his, which I sadly can’t find, in which he was asked how he knew what was good or not good.  He graciously claimed that he had no idea what would catch on and be a hit and what wouldn’t.  What he did know, though was emotionally what connected with him–and he had some funny quote about how he felt a tingle in his chair when a movie really grabbed him.  This ‘a**-grab’ was the thing that told him whether the movie was good or not.  A totally emotional, non-scientific approach.

In the startup world, there is an element of this that’s important.  Sadly, this is sometimes overlooked.  VCs are looking for massive returns and low friction, etc.  Entrepreneurs are looking to make meaning or build something people want, etc., etc.  And while both of these points are useful to think about, at some point, you had better look at a business and be emotionally drawn to it.  At the end of the day, whether you are an investor of money (a VC) or an investor of time (a founder or employee), its important to contemplate whether you think the business has any emotional draw to you (or anyone else).

If you don’t feel the pull, that’s fine, the business may still be a monster, but I’d say stay away.  The work is too hard, the days too long, the competition too fierce for you to be ambivalent on the emotional draw of a business.

More often than I’d like to, I see businesses where teams have built a solution to a problem that does not grab me (or often, their founders) emotionally.  If you love your business, and I don’t, that’s fine–s*** happens, and that’s fine.  If you don’t love your business, trust that others will know.  In that scenario, why do that.  Let it go, don’t settle.  Find the business that gets your spine tingling and give your all to that.

Welcome back to blogging.

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Can You Handle the Truth? Advice for Founders

Always tell the truth, its the easiest thing to remember. — Glengarry Glen Ross

I have started my second semester at the Founder Institute, Adeo Ressi‘s awesome incubator.  It has been a blast so far, in my view, a lot of really strong founders wiht great, viable business ideas. It has been a lot of fun to be involved, and it is as always humbling to have smart, passionate people asking for my input.

As it is still early in this group’s process, some of the ideas are a little earlier on, still in “ideation” (terrible word) mode.  This is of course a natural state of being in a startups life, that early stage when you’re still not even sure you’ve got a good idea.  Its an exhilirating time–you’ve not made any mistakes (yet) and the world seems ripe to take on your vision, while at the same time, you definitely have those soul-shaking moments of doubt as to whether you’ll ever be able to turn your idea into reality.

Int this stew, founders will come to me to ask my advice on their idea, and I’m happy to try to take the time to listen and provide a few minutes of helpful input.

A question I have had and answered for myself is how hard core or harsh to be on someone’s idea when it is still on the drawing board.  Although it certainly has its risks and drawbacks, I’ve decided that this is a time to be very blunt and hardcore.  The risk is that this approach dissuades someone or that it gives them an impression that I’m a jerk.   This is the last thing any founder wants to become–the startup world is too small afor people t get such an impression.

The counter argument is that by being hard core you toughen up a founder, you help him or her focus on the key challenges in their business, and  at an extreme, you convince the founder that the idea is not worth investing time and life in.  At the ideation phase, the costs of switching an idea are low.  I have become comfortable with this being on balance the preferred approach–the pain is worth the value.  I also try to remind the founder whenever I do this that my opinion is just one, and I’m certainly perfectly happy to have the founder prove me wrong and make a boatload of money doing just that.  In other words, its not personal, and I’m hopeful that it does help.

I have come to believe passionately that this is the only appropriate response for founders asking for advice.  My input is not costing anything, and if I’m off by a mile, there’s no reason that a founder should listen to me.  You asked and I answered.  No harm, no foul.  Totally makes sense, right?

Right.  As founders we should all be pushing each other in as hard core a way to make our businesses kick ass and take names.  Give the advice, hit hard.

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The How To Guide to Naming & Branding for Startups

This week I again had the pleasure of speaking at the Founder’s Institute’s sessions on Naming and Branding.  This is the second semester for the Founder’s Institute, and I saw a lot of great improvements from what was already a strong first semester. 

The slides I presented this January 2010 are here:

The slides are pretty self-explanatory, so I won’t go through them here.  I’ve also spoken about this before on this blog here.  In this post though, I’ll respond to the notion that I heard in one session which was that the name of your brand or company really doesn’t matter when you are starting out.  The argument (I think) was that there are many other issues to focus on, and that any name will do. 

While I agree that a founder can’t get so caught up in naming that the vital stuff—getting product built, getting customers engaged, etc.—I disagree strongly with the idea that a company or product’s name doesn’t matter.  For startups or early stage companies, I think this is even more important.  Here’s why.

First off, when you’re just starting the only marketing you’ve really got is the name and brand of your company.  No one knows who you are.  No one has ever heard of you.  When you tell them you’re name, some neurons fire in their brain and they have a reaction.  Are they going to want to lean in and see the demo or are they going to ask “How do I spell that?” or “Say that again, I didn’t hear you.” 

Here’s a concrete example—try recruiting a rock star A++ engineer with a crumby name.  The types of people you’ll want to recruit, I contend, will respond like anyone else.  A crumby name, without a concrete sense of what brand you’re trying to build, will be uninspiring or confusing to a rock star A++ engineer, as with anyone else.  I’d say avoid it. 

My philosophy with startups is simple: When you are all by yourself, you have to use every tool at your disposal to increase the chances of success.  Taking that philosophy means you have to push forward on anything that can help.  I contend your company’s name can help in important ways, beyond recruiting your star engineering talent. 

How can your company’s name help?  Your name can do lots of things, but to me one of the keys is that it can set the competitive landscape to your advantage. 

Here’s my current favorite example from Niman Ranch.  Niman Ranch is a maker of all natural, humanly raised meats.  When they entered the hot dog market, notice the name they chose.  “Fearless Beef Franks,” is a great name for them—it totally positions Niman’s offering relative to their competition.  Niman is a premium priced provider—this name makes it totally clear why their hot dog will cost more per pound than one from Oscar Meyer.

In closing out, I’d say sure you can succeed without a great name, but why would you want to? 

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Working with VCs part 2: reverse due diligence

Earlier this week, I posted part 1 of a currently 2 part series on working with VCs.  As I mentioned there, and as I’ll repeat basically any chance I get: working with venture capitalists isn’t summer camp.  It shouldn’t be.  My personal experience and view is mixed–I’ve had great experiences and some bowsers.  But as I’m generally an optimistm, my basic view is that you’re served best by approaching the relationship with a well-grounded, objective perspective.  Again, this is business, not summer camp; you should know this as the venture capitalists with whom you might work certainly know this.  Not a ding on them, just the reality that you and they should share.

Alright so this post is about tips and tricks to drive reverse due diligence.  In other words, these are the questions and steps to take if you actually get a venture capitalist involved and you want to research whether they’re worth partnering with in building a company.  Feel free to suggest other ideas in comments.  FWIW, these are my concrete ideas and steps.

First, probably the #1 most useful data point would be a VC working with repeat entrepreneurs who’ve had sizeable exits in the past.  Founders who’ve achieved exits previously are the “A-Listers” of the Silicon Valley star system.  The Max Levchin‘s or Kevin Rose‘s are the Tom Cruises or Tom Hanks of Silicon Valley.   To a degree, they have a choice in working with the VCs they want to work with.  A successful founder who chooses to work with the same VC again is a signal that that VC is solid.  (Otherwise, why would the founder keep working with the person?)  Ask the VC which founders he’s currently working with, and research their track records on this specific dimension.  I’ve met and gotten to know a few VCs who can point to successful rockstar founders who continue working with them–these VCs are the guys you want to work with before anyone else.

Second, find out if the VC on your deal is working with founders on a repeat basis who did not have an exit.  Very similar to the above, except with founders who didn’t exit.  This is somewhat interesting, in that it conveys that both parties still think enough of each other to work together again.  There’s a slight flag here that you should check out, but in generla I’d interpret this as a positive.

Third, ask the venture capitalist to get intros to the founders he’s working with currently, and call them up.  Ideally you meet these folks in person, and you really get them speaking frankly.  This can be easier said than done, but you’ve got to do this. Here are the questions I’d ask them:

  • Please describe your experience with them in depth.
  • What is the best thing that has occurred in this experience. (This should be concrete.)
  • What is the worst thing that’s happened.  (This should be concrete. )
  • If you were to have a successful exit and you could work with anyone, would you work with this person again?
  • What is the biggest and most significant impact this person ahs made on your business?

The purpose here is not to drive a gotcha type conversation.  You are just trying to get information as clearly as you can on the pros and cons of this specific VC.  I consider this must do work.  What I’m providing here is just a basic set of guidelines.  For your speicifc business, there will be a whole host of individualized issues that you need to drill in on.  The point isn’t so much that there’s a single list; its that you’ve got to go through it.

I’ll probably add more to this list as I mull, but here I thought I’d take the approach of getting this out there and then adding as I think further about it.  Comments welcome.

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Working with VCs part 1 : its not summer camp (nor should it be)

This week in the geekosphere, this presentation on venture capitalists has been making the rounds.

Its funny, and as an entrepreneur who’s met and worked with VCs, I can relate to this.  Some are clueless, herd following clowns, and there’s no small amount of glee we all take in poking fun at those folks.  Many aren’t, though.

Irrespective, if you’re working as an entrepreneur and you want or need venture folks to build out your company, then it’s important to have a clear-eyed, rational view of what venture capitalists are doing.  Having this perspective will help you more effectively set your own expectations, and ideally, will help you do a better job in working with them.  This thinking led me to a two part post.  Part I, below, is meant to provide a different perspective from a founder’s poin

t of view on VCs.  I think its useful for founders starting out to have this perspective.  Part II, which I’ll get to later, is about how I’d suggest doing reverse diligence on investors or VCs–who do you speak to and what questions do you ask them–this is more concrete.

So, Part I has the risk of labeling me a VC apologist, a kiss-ass. Whatever.   I’ll share this not because I think VCs need defending.  Rather, I think its important for founders to have a rational view of VCs, in order that founders are thinking clearly about what VCs can do, and how to think about working with them.   If you’re a good entrepreneur, you need to be thinking clearly and rationally about what you’re doing.

Here are the key 3 things I try to remember when I think about venture capitalists.

1. At their core, VCs are the money.  VCs, at their core, represent the money.  At times and at their best, they represent more, but at the end of the day, they are ‘the money.’   This is not meant as a negative–within the sphere of ‘money,’ I view VCs as useful and constructive. They’ll try to be useful, and they’ll (hopefully) try to remember that they’re not magicians.   They want to help, but they’ve got 7 or so boards to work on, in addition to other companies to look at, in addition to raising money themselves.  They want you to succeed and they want to spend less time worrying about problems, more time helping you accelerate, recruit, get press, etc.

They’re way better money than any other institutions out there.  They’re generally not like private equity funds–looking to lever up and sell off! They’re not (generally) in the turn-around business, looking to squeeze costs, downsize, etc.  In general, they are looking to build companies that swing for the fences–they want ideas generally big and wild and possibly able to make an outsized return.  They may do self-interested things, but they’re going to be more aligned with you than any other money you’re likely going to find in the institutional private equity space.  (If you think VCs can be difficult to deal with, try working with guys at hedge funds to finance your business.  Good luck!)

2. The water-finding stick pitch. VCs are funding ideas sooner than most any rationale investor would–that’s why they’re in the business.   While VCs as a group will have different focus, stage, etc., there are many instances where they will give money to people who have nothing more than a powerpoint, a cocktail napkin, sky-writing, whatever.   Some of those who get funded have no professional track record to speak of, with unproven models, unproven businesses.  (!)  Think for a second how crazy that sounds.

Divining Rod
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Here’s how crazy I think this sounds.  When I was a wee pup growing up on the farm in Latrobe, we once needed a new well.  (Ours had run dry, and we were literally out of water.)  We called up the well digging people, and out they came.  Their gear consisted of a huge drilling type rig to drill the well, and a ‘diviner,’ a guy who figures out where to drill.   The diviner walks around holding a Y-shaped stick by the Y’s ends in his hands.  The bottom of the Y-shaped stick, the theory goes, will point down to the ground when he walks over a spot in the earth where there is water.  I’ve not yet seen any scientific explanation for why this exists.  All I can tell you is that it worked.  Within about 15 minutes, he’d identified 2 spots, and he suggested one that hasn’t run dry in the 20 years since that well was drilled.

So that’s a cool story, but the epilogue is what’s relevant to this.  After the drill diggers had left, my dad, an entrepreneur in his own right, shook his head and asked “could you imagine those guys going to a bank looking for a loan?  Their pitch would be: ‘we find water using a stick!'”

If the water finding stick guys showed up on to VCs, VCs would at least want to see a demo before telling them they were crazy.  Every other institutional money source would likely just throw them out of their office.  Remember that.  I remember that and think it’s pretty awesome that I live in the US where there’s a whole industry of folks who will do that.

A Scout assembles his troop at a summer camp.
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3. “Its not summer camp.” I once worked on a turn-around situation in business.  It had a bunch of difficult people issues involved.  My boss at the time and I were talking about some of the moves, and whether the team would be comfortable with all the changes.  My boss said something that I say a lot on this topic: “It’s not summer camp, Jay.”  He meant it both for me and for the team, and he meant that I needed to get tough, and the team did as well.  And he was right–we’re responsible to share holders, customers, employees, etc.  Getting a VC involved does not mean that we all spend time making hot cocoa and gazing lovingly into each others eyes.  It’s a business transaction, and founders need to deliver.  You’re not in summer camp.

Now, with that said, know that there will be days that stink.  Investors will move goal posts or get squirrelly.  Commitments won’t quite be met in the way that we might have thought.  Etc.  And you can get embittered, or you can pick yourself up and realize point one and two above–these guys are the money, and they’re funding water-finding stick businesses.  On the whole, with whatever else goes south, I feel generally pretty lucky to have the opportunity to work with smart people to build a kick ass business.

So those are my 3 key perspective points that I’d share as you think about building your business and working with VCs.  Its high level, but I find these 3 points useful to remember.  Stay tuned for Part II, where we talk more concretely about how to run a diligence process on vetting and double checking the investors you might be workign with .

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My Founder’s Institute Talk on Branding & Naming Your Startup

Last week, I had the pleasure of speaking as a Mentor at Adeo Ressi’s TheFunded’s Founder’s Institute with entrepreneurial superstars James Hong and Bryan Thatcher.   image

First off, before I get into the topic, let me say that I think the TheFunded Founder’s Institute is innovating the approach to startups in an important way.  The approach is a mix of company building philosophies.  It’s one part bigger hammer–that is bring in lots of smart people as founders.  It’s also another part strong social networks, connect those founders to each other and to experienced, proven entrepreneurs.  Add top-tier, discounted, startup services (legal, accounting, etc.) and that gets at crux of the approach.  The new stock class—F-Class—which Ressi’s introduced is also super interesting.

There are a lot more unique details to how Ressi’s going about this, which I’ll not go into here.  But suffice to say, it is both empowering for entrepreneurs and it has a bunch of detailed thought behind it.  Ressi’s vision is big and broad.  It is exciting to be a part of, and I’m eager to help it succeed.   More concretely, I wish I had had access to such a thing when I was trying to start out as an entrepreneur.

Ok, so that’s the Founder’s Institute, now onto what I was talking about when James, Bryan and I spoke last week.  Our topic was Naming—as in, you’ve now figured out what customer problem you think you’re solving and what you want to do, now what do you call this thing?

This is a fantastically rich and interesting topic.  It’s also, IMHO, super super important.  When you’re a startup, your name is about the only marketing you really have at first.  Also, everyone—customers, potential employees, and potential investors—will ask you about your company’s name.  So whatever you name and brand your company had better be good.

My slides from the presentation are embedded here (hat tip to the folks at Igor International, who’s free naming guide was very influential):

(Shared with permission from TheFunded Founder’s Institute.)

It was a good discussion, and my sense is that this provides a useful prescription for startups thinking about what to name their company and how to approach their brands.  Some key points for reinforcement.

Having a process for naming helps.  What I think is particularly useful about this approach is that you can put numerical scores next to how you think about names.  This enables you and your team to have a concrete discussion about why someone likes versus dislikes a certain name.  This is important, as it enables your team to come to a more objective decision, as opposed to just who yells loudest.

Think BIG picture first, then worry about finding the .com or URL that’ll work. Following my talk, one common theme in speaking with people afterwards is that I think many people get hung up on the challenge of finding a good .COM URL that’s not already been picked up.  While certainly a challenge, I think that worrying about this tends to drive entrepreneurs to small thinking.  You’ll have to work through it, but that’s an end point, not the beginning.

As I’ve said in other posts—as an entrepreneur, my advice to other entrepreneurs is to think big in everything you do.  So when it comes to naming and branding your company, think big.  Go for a big name, figure out what that makes sense and helps position you strongly relative to your potential competitors.  Figure out a name that really delivers on the strategy that you’ve put in place.  Get that strategy right and solid.  Then you can go and figure out the more tactical issues of what the URL hunting strategy needs to be.

Commit to going through the process.  The other thing that I’d encourage people to do is really commit to going through the process that I’ve described in the PPT deck.  I’ve met with several companies over the past year who’ve listened to this process, ignored it, and then have ended up hiring a naming consultant to basically help them go through the same thing.

Acknowledgments to the folks at Igor International. Igor International have open sourced their naming guide, which is a great thing.  My deck basically walks through how I used that free information to secure Moonshoot, an awesome brand name, IMHO ;).  The tool Igor’s provided is for frugal founders like us a tool to go figure this out on our own.  Invest the time to commit to doing it.

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