What I Learned About Raising A Seed Round, From Cutting My First Check

Over the last 10 years, there has been a ton of information out there about what it takes to raise a seed round, or money in general. I’m not here to rehash the great advice that’s already out there - check out: Mark Suster, Jason Lemkin, Brad Feld, et al. I’ve read tons of it and used that information to pitch investors, as well as advise founders on how to pitch investors and it’s truly applicable, sage advice. However, recently, I made my first angel investment and I wanted to share with you my thought process from the other side of the table (*tip of the hat to Mark Suster*).

*Get a warm introduction from a high-quality contact in the investor’s network* 

In this case, the introduction came from Jamie Hurewitz. Jamie has deep startup experience as a head of legal at high-growth, venture-backed startups, advises many startups and she’s my wife. This past summer, Jamie was advising a cohort of startups through an industry-themed incubator. Out of curiosity, I looked at the startups and soft circled the ones I liked. 

• Would I invest in the market / space? Check

• Do I believe in the problem & solutions? Check

• Is the intro coming from a credible, highly-qualified source in my network? Double Check

*Build Momentum*

Periodically, Jamie would provide me updates on the startups. I became excited to hear the progress and began making some introductions within my own network. It’s during this phase that I began asking if any of the startups were raising money and if I could attend the demo day.

• Is the team making progress / hitting milestones? Check

• Am I excited about the progress they are making? Check

Then came demo day. I was very excited to hear one particular company’s pitch, until they started. They lead with the dreaded, “We just closed an oversubscribed round.” For F^cks Sake (‘FFS’) - this does happen, but man is it a shot in the gut. I shook off the gut punch just in time to hear about more momentum; I was simultaneously sad that I wasn’t going to be a part of this company, while simultaneously being very excited to have spotted and seen the early journey of what I believe is going to be a very exciting, impactful and successful company. Then, the company continued to share milestones that made me even more bullish on their future success. I suggested that Jamie reach out to the company after demo day to ask if they might still consider taking on additional investors. She said she would.

*Are they already on the path*

• Is this company going to be successful without my money? Check

• Am I able to add value, beyond money, to the company? Check

• Are they raising money? FFS

Over the next few weeks, I expressed to Jamie that I was feeling sad that I wasn’t able to get in on the seed round of that one particular company and asked if she had reached out to them yet. Being the busy woman that she is, unfortunately to my dismay, she had not. However, it just so happened that Jamie’s relationship with the founders was ongoing and they’d been exchanging emails. Unbeknownst to me, while on a family e-learning, Covid retreat, in one of their correspondence Jamie mentioned my disappointment for missing out on the round - it was at that point the CEO replied that they had a small slug available in their syndicate, if we were interested. 

Next I heard Jamie loudly call out from across the house, “Matt come here, quickly!” Instantly, I was slightly panicked - I was expecting anything from a spider sighting to bloodshed. Much to my surprise, she was excited to tell me we got into the round. At that point, I told her to tell the CEO we’re in. She replied, “I already did”.

As a non-leading, seed investor, there isn’t a lot to the deal - even as a seed-stage lead, diligence is very limited. However, I was surprised to experience that “Just Take My Money” moment. It may seem like a rash way to make an investment, but after talking to several personal friends that are angel investors, apparently it's more common than you might think.

As a founder raising early-stage money, my advice to you is to be more focused on creating that “Just Take My Money” / “I’m lucky to be in this deal” feeling among investors - and the best way to do that is make the kind of ongoing progress that shows investors that you are already on the path to success, with or without them. If you can tell that story, the money will come. 

If you’ve had similar experiences as an investor or founder, I’d love to learn about your experience in the comments below.

Yahoo! Fix? - It's Not About the Chief, It's About the Indians

Yahoo is all the rage again, this time it's b/c Carol Bartz is out and everyone has an opinion on how to fix Yahoo's problem...For all of those who think a product visionary (Steve Jobs) is the answer...it's not about the chief, it's about the indians.  The tech community talks a lot of shit about how Yahoo! is done.  They aren't.  They've got the biggest email user-base in the US (where they do well in content), are in fantastic positions in several markets abroad (in content and email) and make tons of money.  The next CEO needs to figure out how to retain, excite and recruit guys like Paul Tarjan (Yahoo! Resignation Video below).

Approximately 2.5 years ago, every day TechCrunch was flooded with who's leaving Yahoo! now articles.  Some people left for Facebook/other startups, some founded their own ventures and others jumped to other tech giants.  People jumping around isn't new or necessarily news worthy.  After all, certain types of people always leave big companies, they just don't fit and can't stay.  Their thrill comes from figuring out solutions, as opposed to executing/maintaining established systems.  With some of those types, even if you have cool projects in the pipeline, a lot them just like changing things up or want to launch their own venture.  On the other side of the spectrum, many people will never leave the company they work for.  They are good / great at their job, settled into their responsibilities and work-to-live, as opposed to those who live-to-work.  There is nothing wrong with either types of employees or their professional proclivities.  What we saw with Yahoo!, and the sign that their culture was broken, was when the movers-and-shakers, the creative/quirky people, the ones who epitomize your culture (the stereotypical company XYZ employee we refer to when we talk about your company) and those management wanted to cultivate into future company leaders, up and left, in droves.  That exodus was the sign the culture was broken and no one with the power to do so cared enough to fix it.  When the culture that brought them to Yahoo! was gone and it became clear it wasn't returning, everything got tainted and they could only stomach it so long, before they left.  

What's left is a money making machine, that's not beyond repair.  However, greatness comes from your companies culture and Yahoo! has to get that back internally, before they can project an external image that attracts the types of people that left, back in the future.

How can they do that?  They have to break a few eggs.  Yahoo! has a lot of talented engineers, why not empower and motivate them to start solving problems?  Yahoo needs to spend a small fortune (how about the $10 million they don't have to pay Bartz for disparaging them?) on an all-hands event that expresses their appreciation for their current employees,  rallies the troops, forces product managers to experiment on their products and ends with announcing a new initiative that rewards and allows individuals to incubate Yahoo!'s future products.  Then, hold a small-group Hackathon, see what floats to the top and support the most promising projects.  Then, hold the hackathons every month (keep them themed.  One month is new features for existing products, then mobile, then deals, then whatever) and keep supporting the best projects.  That will build morale, buzz and excitement & that's what'll attract others to Yahoo!.  Oh yeah, you'll probably get some great products / features out of it too (and don't forget to tip your innovators).

Kinda sounds like a place I'd like to work.

  

The Myth of the Early Stage Pitch Deck

Do you know why there is so much information about how to craft the perfect early-stage pitch deck?  Because, people believe a good deck will get them investment...the secret is, it won't.  To make matters worse, it's damn near impossible and let me tell you why.

First of all, no matter how good your slides are, you're only guessing what the person across the table wants to see.  I realize that many VCs, like Sequoia and Dave McClure (500 Startups) via How to give a VC a Hardon, tell entrepreneurs what they want to see.  However, that's just a guideline at best.  Depending on whom you actually get face time with, even within the same firm, they all have different experiences, knowledge bases, skill sets and triggers...not to mention getting VCs interested is about getting them excited, not-not boring them to tears.

Second, public speaking is hard.  Most people can't land a joke successfully when all eyes are on them.  Think about how many conferences you've spent staring at your phone or picking at your terrible meal, instead of listening to the speaker.  In the world of entrepreneurs pitching VCs, I guarantee that no VC has ever invested in an entrepreneur they've tuned out.  But, don't worry.  You don't need to spend years perfecting public speaking.  But, before I tell you my thoughts on what to do, I'm sure some of you are wondering, "How do you know if I'm a talented speaker?"  If you haven't spent years dazzling crowds, or if you don't feel guilty about all the great events you have to turn down speaking requests from, it's unlikely that you are a great public speaker.

The good news is, you don't have to be.  Check out Sergey & Larry at early Google.  The secret is to let your passion come out.  Focus on what you have going for you, which is the problem you're solving, your solutions to the problem (ie product) and the empirical evidence you've gathered that tells you it's going to be a winner.  The best pitch meetings I've ever had started with a demo (core use case, not EVERY SINGLE FEATURE) and then I shut my mouth.  The interested ones wouldn't let me through the demo without lots of questions and comments (that's a good thing).  After you get through the product / use case, then it gets down to the evidence.  This is where you should use your prepared slides.  If you get through the details and the conversation turns turns to "How much are you looking to raise?" or "What can I do to help?", that's the best possible outcome...no pitch from a deck required.

The caveat is if you aren't pitching the right person in the firm, the aforementioned doesn't apply.

Then why do so many people ask for decks?  Theoretically, a deck is faster to thumb through than a executive summary and you can direct submitters to touch on important topics.  All that means is, if you are part of the unfortunate masses that haven't invested the time into directly networking with investors or people investors respect, when you get put in the never-empty inbox, you have a better shot at getting thumbed through.  But, do you really want anyone seeing your slides un-narrated?  NO!

If you get a seat at the right table, let your passion, hard work and external validation shine through.  There is nothing worse than having your pitch stopped or watching people you've spent months trying to get to-check their email.  Realizing you blew is like a punch in the stomach.  Pitch decks are only for products that have gained traction (specifically in the minds of investors).  If the person you are pitching isn't already a fanboy, and they're usually not (odds are they haven't even looked at your product, even though you are on their calendar), you have to make them a believer.  To do that, you must make them believe, in this order:

1)  users will use it.
2)  that someone will pay for it.
3)  that they can make a big return by backing it.

Most investors invest with their gut and justify with facts.  Once you've crossed the threshold of worthy of their time (their most valuable resource), they'll be more forgiving.  However, for most of us, running them through a slide deck during your 1 bite at the apple, isn't going to do it for you.  The good news is, now you know that is.

What Startups Can Teach Big Companies About Hiring

I've read so many posts about interviews.  Whether you are trying to learn what questions to ask or how to answer the hard questions, the practice seems to be converging towards a standard song and dance, as opposed to a true assessment of how an individual will meld with your company's culture and what type of value they will bring to your company when they get there.

First, screen candidates for actual business needs. Every interview should have some standard for general competence, because we've all seen resumes that take liberties.  However, if you are hiring a developer / engineer, give them a real world problem and ask them how they'd solve it.  Better yet, tell them about problems you've actually encountered.  Then, ask them how they would go about solving the scenario.  Then, have them start coding it.  Throw them some curves on the fly and see how they deal with it.  There is more value in seeing someone psuedo-code a solution (free from a scrutinizing eye saying "that'll cause a runtime error") to How would you programmatically parse a sentence and decide whether to answer "that's what she said"?   than there is in knowing the difference between obscure algorithms (for 95% of your engineering team).

Next, interviewers are sales people.  There job is identifying hot leads and figuring out how to close.  It is a skill, so don't send them out unprepared.  Every interview I've been on, as a candidate, ends with me asking:

"What is your company / group's short-term goals?

"How do they measure progress towards achieving those goals?"

"What does your company value and how do they live those values?"

"Someone from your company said your company is looking to move in direction X.  What tangible steps have been taken to support that directive?"

From a startup perspective, those questions are critical to recruiting people and keeping them happy when they join your team.  As an interviewer for a larger company, you should make it a point to mention these things; they aren't just important for startups trying to recruit.  I learned to ask those types of questions because the information never comes up unprompted.  Surprisingly (or not), most of the time, the people conducting interviews can't answer those types of questions anyway.  Not bringing those types of things up, and certainly not being able to answer those types of questions, is a sure sign that your house isn't in order.  And your house has to be in order to attract the right type of candidate.

That leads me to my final point. HR representatives should know the open roles they are responsible for, the teams looking to fill those roles and the projects they are currently working on, cold. However, they should also know what other open reqs are out there AND have a standard for finding roles for 'the right people'.  All too often, candidates interview for a position and would be a better fit somewhere else.  It's a miscarriage of HR's responsibilities not to be able to spot this when it happens.  Since most larger companies have an arduous process for requisitioning new personnel, I'll stop short of saying that a great company always has a place for talented employees.  But, they really should.  At a small startup, the people trying to build a company based on a vision are conducting the interviews.  They would never let 'A' talent out the door because the role wasn't a fit.  At a larger company,  recruiters should pretend that the CEO, COO or SVP of something or other, is behind a two-way mirror.  Believe me, 'A' talent in a new role is better than experienced / I fit the job description perfectly 'B' talent every day of the week.  And let's face it, you have to hire 'A' talent when you find it.

It's Not Them, It's You - Why You Can't Recruit Top Engineering Talent

Recruiting anyone worth having on your team is hard.  But, as a entrepreneur, you won't get very far without being able to do it.  Over time, I recruited a technical co-founder and several engineers / designers (albeit only part-time).  I'm almost embarrassed to tell you how long it took me to figure out what it takes to get them to give up what little free time they do have to spend it working on your startup idea.  Instead of airing my own dirty laundry, here's an approach that I've found very effective when recruiting engineers.

I tell everyone in the startup world that ideas are a dime a dozen, work on the idea that is meaningful to you (work on the project that you would use A LOT).  The problem is, it's unlikely the problem that drove you to start a startup will be more than 'interesting' to most engineers...especially the engineers you want.  However, interesting is a good starting point, not as good as "I've known this person X for years and we've been looking for an opportunity to work together", but it'll do.

What makes an idea interesting to you is the use case.  Once you figure this out, I encourage all non-technical founders to spend time learning to code a bare-bones v.0001.  Learning to code (a little bit) does a couple of things:

1) you get some cred w/ the engineer
2) you understand the lense through which your recruit sees the world
3) you understand a snapshot of all the work that goes into some business guys bright idea for a new feature 4) you develop genuine admiration for the skill set it has taken your potential hire years to develop

Then, get it in front of a potential hire.  At this point, you must treat the potential hire like the prettiest girl at the bar.  Get them interested, using as few words as possible.  Let them play with the product..  Ask them the some key questions.  What do you think?  Given what's going on with the web today, what would you build next?  If you've had users, give the engineer user feedback.  If they are interested, you'll see the sparks flying.  You'll know it's going well if they start talking, hypothesizing, building Rome and using the pronoun 'we'.

Engineers that join early startups has an uncharacteristic (to their field) risk profile and you have to nourish their inner desire to do more than just code.  And guess what, the engineers I've worked with have WAY MORE TO CONTRIBUTE than just code.  They can smell a whartonite-seeking code monkey a mile away.  Don't be that guy!!!  Any early members at a startup is a utility player, the more they bring to the table, the better off you will be.

FYI, being able to recruit goes a long way towards building a team and moving your project along.  Which is to say, it's a major milestone in terms of showing a customer / investor you can get stuff done.  It'll also stop you from ever having to say, "I'm raising money to hire 3 rock star engineers from company XYZ that have already told me they'll quit their job once I can pay them X."  If you don't already know, the aforementioned statement is second only to, "You'll need to sign an NDA before I can tell you about my idea," on the list of things to say to get thrown out of a serious conversation about startups.

Only N00Bs Ask For Advisors / Investors

I'll preface this post with the fact that I spent the better part of 9 months reaching out to investors for money and anyone who had done anything remotely significant in my project's space asking for advice.  During that time, I found that there is a lot of goodwill in the startup/investment community and lots of great folks who field thoughtful responses to enthusiastic neophytes b/c they remember what that feels like.  In my case @joshk, @jayadelson, Kamran Pourzanjani and a few others, gave me way too much of their valuable time (based on a cold email / chance meeting), when I truly didn't deserve it...If you find yourself in that position, make sure you are respectful of how you use their ears when you have it, or you will certainly lose it.

The point is, investors invest and thought leaders advise (and sometimes invest too).  As an entrepreneur, you need both types of people involved in your startup, so it's natural to identify targets and phrase 'the ask'.  From my experience, that approach doesn't work.  But, I have found that the following approach works for both types of people.

Build a product, an MVP like I mentioned in my previous post, and get people using it.  Once that happens, try to get face to face with your target.  You should note that they probably won't take a meeting if they don't have a warm intro from someone they trust (ie someone that made them money).  So, go to the events they go to.  Politely introduced yourself, use your one-line pitch and show them your product.  Then, here's the really important part, SHUT YOUR MOUTH AND OPEN YOUR EARS.  If they aren't interested, they'll let you know.  If they are interested, they'll start talking and that's a good thing.  The most valuable commodity investors / advisors have is time.  If you are getting it, make sure you don't fuck it up.

Investors are highly intelligent and have tons of experience.  If they are interested their wheels start turning right away.  They'll have suggestions and questions, make assumptions that may or may not be true, and they'll give you an opportunity to demonstrate to them that you are the person that can take an interesting idea and turn it into a big business.  If all goes well and you jive, which is to say if they can believe they can convince their partners that you are investment worthy, they'll ask if you are raising money.  It's their job to invest.  They'll assume the reason you are talking to them is to raise money (b/c it is), so you don't have to ask.

Advisors are a little different, depending on their background / experience.  When talking to them, approach them in the same way I mentioned above.  If they are interested in you and / or your product, they'll come out and say, "What can I do to help?"  At that point, you don't need to ask them to advise you, b/c they've already offered.  FYI, you don't need to offer advisory equity to most people, especially if you haven't raised money / have a formal board.  As a matter of fact, I'd caution you as to anyone who says they'll advise you if you give them X.  Also, advisors are just that, so use them respectfully.  Especially at first, limit your asks to things that can be solved over coffee, introductions, etc.  After all, most advisors worth their salt are probably running their own companies / departments and advising multiple other startups, while trying to maintain some type of personal life.

Remember, you don't need to ask.  

Just F^cking Build It & Send It!

     As a nascent entrepreneur, my team and I have been knocking out projects for about 1.5 years.  Some better than others, but we have a few minimum viable products (MVPs) under our belt (and from my experience comes my .02, buyer beware).  With our latest project, I found that we were trying to build Rome.  This was a mistake we made with our first product, it was pointed out to us by @Votizen's David Binetti and we've tried to avoid doing it again ever since.  If for no other reason then to remind myself, "JUST FUCKING BUILD IT & SEND IT" & "DON'T BUILD ROME".

     There is a huge emphasis on perfecting your pitch, the elevator pitch, the my company is X for Y and so forth.  There should be as much, if not more, emphasis on building just enough to see if your product has a market / delivers value.  In our case, we have an integrated solution for e-commerce.  We have to add functionality to existing systems in order for our application to work.  So our barrier is higher than most.  But, if you are building a social solution, my advice to you is think ABACUS (ancient mathematical tool you played with in grade school).

     The abacus was around for thousands of years because it got the job done.  Later it was replaced by the slide rule, then calculator and now the calculator app...but it got the job done so people used it.  When you deliver value to a group of people in need, some portion of that group will use your product.  Then, once you've attracted some...focus on making it better to attract more.

     If your team is arguing about whether or not you'll lose more people b/c you don't have multiple login services setup, just get Facebook going and move on.  If you don't have Facebook and Twitter sharing setup yet, guess what?  If your app sucks, people won't share it anyway...time wasted installing those buttons / delaying your launch is time you'll never get back.  And don't add any 'You Can Also'.  Let me repeat...NO YCAs.  As a startup, your product does one thing.  If no one likes that one thing, take it down and do another.  No user will look past your first crappy offering to try some other (crappy) thing.  You have like 5 seconds to deliver value...otherwise they are gone forever.  First time users of web / mobile apps don't have time to figure stuff out...it's your job to make it so simple they don't have to think twice about how to use it.  When you are big you can add other stuff, when you are a startup you have to be focused on one thing at a time...