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.

Scratching My Own Itch - iPrompted

When I shutdown my last startup, all I wanted in this world was a cushy, corporate job. You know the kind. 20+ PTO days per year, plus company holidays, 401(k), cash bonus, maybe a little stock. I wouldn't have the ball, but I'd make a nice living and recover from 2.5 years of self-funding my dream. I was tired, defeated and just wanted a regular job.

So, that's what I did. Along the way, I got divorced and re-married. My wife is a fierce planner, list-maker extraordinaire, organized and efficient, whom I infected with the startup bug. She's currently the head of legal for Gitlab. Me, ADHD, jack of all trades, that gravitates towards Jeff Atwood's Top Three Things, currently managing Enterprise Information Protection at Best Buy. We have a blended family and between hers, mine and ours we have four children, from 14 (with ASD and ADHD) to almost 3. Needless to say, We're always running to or from somewhere.

My wife would describe me as well intentioned, but forgetful / oblivious at times and she's right. If she mentions something to me, the odds of me completing the task decreases at an exponential rate, after the initial request. Frustratingly, for the both of us, there are tasks that she has to remind me to do over, and over, and over and over. When her frustration gets big enough, it makes my top three and gets done. However, it's at a cost to our relationship.

It turns out I'm better suited to build a solution that solves this problem for millions than I am at solving it for myself. After all, if I could keep a calendar and make lists, I wouldn't be in this predicament in the first place.

So, I was telling a friend about my idea for a solution to my problem and he saw a lot of himself in my predicament and asked if he could build it with me. And that's what we did.

If my wife only had to ask me once, could technology make sure I get it done and then close the loop? Is there a tool that the organized people in our lives can leverage to make sure we get done what we need to? I want to make the most out of my time and not let down those around me, especially the ones that depend on me. I couldn't find something that scratched this itch in a way that resonated with me, so we built it.

Whether you are tired of dropping the ball or tired of having to remind someone in your life over and over again to do something, check out iPrompted and leave me your feedback in the comments.

My Order Shipped In 2 Hours and 21 Minutes...And Not From Amazon

My amazing girlfriend and I have been planning a trip to Thailand and it's rapidly approaching. Since we're going to be spending a good amount of time near the water, she mentioned investigating an underwater camera. The first time she mentioned it was the afternoon of 3/12, a Wednesday. On 3/13, a Thursday, she had clearly done some more research and was circling making the purchase (I'd recalled seeing similar behavior with a pair of really cute winter boots). So, during the late morning of 3/14, a Friday, on the way to the gym, I decided to surprise her with an underwater camera. But, my cleverly-orchestrated, surprise gift would only work if I could get her the camera before she bought it herself.

**It's important to note, she lives in Minneapolis and I was in California at the time (KW - clarification)**

On the way out of the locker room, I opened up the Best Buy Android app, found the Go Pro Hero 3 Silver Edition & and SanDisk 16 GB memory card and I bought it. Then, it started getting weird.

At 11:20 AM, on Friday, I got the following email:

That's nice, and while it's generally accepted that a website sends an email on confirmation immediately following an order, I was surprised that got one from Best Buy (and I work for BBY).  Now, I usually buy research online and buy in-store, so this might not be news to regular bestbuy.com online shoppers. But, it gets even weirder.

At 1:41 PM, on Friday, I got the following email:

As a customer, I'm was shocked, in the best kinda way. I did the math to discover that they processed my order and got it shipped in under three hours. From the perspective of a customer, that is a pretty amazing experience (I was delighted). But, as an employee, i got to see how an organization's hard work pays off, 1st hand.

Now that I was focused on following the bread crumbs, my investigation didn't stop there. I clicked on the tracking link, which is blacked out above, and starting following this package, slowly at first, but more fanatically on the day of delivery. The tracking table, in its entirety, is here:

After clicking on the "What's This?" link, I learned a few things:

1. Order Processed: Ready for UPS: UPS has received the electronic transmission of the shipment details and billing information for this shipment from the sender. Once the shipment is moving within the UPS network, the tracking status will be updated.  - A 3rd party was able to verify receipt of the completion event that BBY shipped this item REALLY FAST, though the verification was done at 3:04 - 3 hours and 44 minutes after order.
2. Origin Scan: This scan is the initial electronic record indicating UPS has possession of the shipment.  -  UPS was in possession of my package less than 9 hours after I ordered it.
3. Delivered: The shipment has reached its destination, and the date and time of delivery have been recorded. In the U.S. and Canada, residential deliveries that do not require a signature may be left in a safe place, out of sight and out of weather. This could include the front porch, side door, back porch, or garage area. If you have instructed the driver to leave the shipment with a neighbor or leasing office, the driver will leave a UPS InfoNotice^® at the delivery address.  - The next business day, after getting home from work and relaxing a bit, my incredible girlfriend had her gift in hand - SURPRISE!!!.

The day of, I was so excited that this was coming together so quickly, that I was obsessively refreshing the tracking page, starting at around 5:30, to see when the package would arrive; not to mention all the excuses I made to excuse myself and check on something (which was really checking for package delivery). And when it arrived, and I got to see her open the box, and it was pretty awesome.

Now "how we do it" is very interesting, but not nearly as important as "that we do it". For more details on our "Ship From Store" program, you can read an article here. The short of it is, we've turned all 1400+ stores into mini-distribution centers that can fulfill online orders and do it quickly. And we're just getting started...I can't wait to see how efficient the supply chain will get over time.

And because my order was for more than $25 dollars, it shipped for free. 

Now I'm a BBY employee, and the views above are my own. However, as a consumer, I was delighted and thought the experience was very cool and worth sharing.

Dear Hiring Manager, It's Too Bad We'll Never Chat

Recruiting has been, and always will be, about people and relationships. However, with all the technological advancements, it's easy to see where that message gets lost. A recent interaction with a recruiter on LinkedIn led me to realize that because I'm not actively looking for a job, the hiring manager will probably never know about me. Let me explain.

What does my profile say about me?

A recruiter reached out to me via LinkedIn. For reference, you can see my profile here. My profile is relatively sparse, especially when compared to most folks. But, my summary is pretty straight forward. I have experience re-thinking traditional business experiences / processes, across industries, and use technology to redesign those experiences / processes. It's somewhat vague, but hey, I'm not looking for a job. I'm currently working at a BigCo, though BigCo does have a precarious reputation in the tech community. I also ran my own startup, worked at another venture-backed startup (though not on my LinkedIn) and worked for a small business. My profile also has a link to my blog and 5 patents pending.

What happened?

One day, I get an email from ScalingTechCo Recruiter, Jane Doe. Jane says,

Matthew,

I came across your profile and interested to learn if you might be on the job market. ScalingTechCo, Inc. is the world's leading marketplace in WIDGETS.I am looking to hire a Product Manager. We are looking for someone that has good experience managing a product in the busy world of the WIDGETS space. Would you be interested to learn more about the role? It's in SHANGRI LA and we do provide relocation assistance

I look forward to hearing from you

Now, this is pretty generic.  I'd really like a message that said something like, "I reached out because I saw that you are working with cutting-edge technologies to solve really hard problems. We have those types of problems and need someone like you to not only solve them, but do so in a way that differentiates us from our competitors (possibly even help us build a team of innovators, like yourself). I'd love to talk to you. Do you have time to chat?" The only other thing I'd be looking for is some insight into some of the problems they are facing. However, it's a first pass, so I'll cut Jane some slack.

My father taught me that there's no harm in listening to a proposal, so I responded with:

Thanks for reaching out. Generally, I enjoy my work and I'm not actively entertaining new opportunities. However, if the role matches my interests and skill set, and/or provides significant career advancement, I'd be open to a brief discussion.

Let me know.

The goal of this email was to get the conversation aligned with my interests and set expectations. Her response was:

Great. If you want to send me your resume, we can start there! I'll see 

what roles I can share that are the most natural fit   

Arghh! There nothing more frustrating than someone pursuing something from you and then levying an action item. Now, I'm sure having a readily prepared resume is a good idea. But, I don't have one. And, in the world of applicant tracking software, a recruiter just wants something to upload it and see what comes out the other end. I get it. But, I asked very specific questions, which weren't answered. Way to make a guy, who didn't come looking for you, feel special. A few days later, I respond with:

I didn't forget about you. I got really busy this week and haven't begun to put a resume together. 

I'm interested in 2 things: 

1) working with cutting edge technology to solve business problems; as you might see from my linkedin profile 

2) moving into product leadership 

I am very familiar with the WIDGET space (my startup was in that space). I'm also a big fan of ScalingTechCo (I used the site to get a WIDGET for a Valentine's WIDGET SPECIAL). Can you speak to whether or not any of the open positions meet either of my aforementioned interests? 

And I haven't gotten a response to date.

Who loses?

First and foremost, I lose. I will never know what job is available and if it offers a better opportunity than my current job. However, I'm happy with my job. The recruiter probably chalked me up as a lead, which might be a metric for her. But, what about the company? The hiring team might be missing out on exactly what they are looking for, or at least in the ball park (though probably not, I'm an acquired taste). But, the interaction put us at a Mexican standoff. I'm not willing to put in the upfront work for a role I know nothing about and the recruiter is unwilling to tell me about the role until I give him/her a resume.

Well, who's job is it?

The best stories of great leaders at great companies are those that go to great lengths to recruit very specific talent into their ranks. Now, I'm not saying that's me. I'll never get a call from Mike Duke, where he pitches me because I'm the guy that can take walmart.com to the next level, as chronicled here. Nor will Jeff Bezos write me a personal letter, like he did to recruit a rising distribution star from Wal-Mart. But, when I was recruiting for a small startup, I had to go to great lengths to make great engineers feel special, just for the opportunity to sell them on my small startup's dream. Unfortunately, that type of interaction is very hands on, so it doesn't scale. But, it does pique the curiosity of people that aren't looking for a job in the first place. 

What's the message?

Recruiting isn't scalable. Great employees, and the rare rising stars, are what build great / scalable businesses. So, if there's one place to put in the most effort, it's in courting the right folks, in hopes you'll filter down to the right person for the job. Now, not every hire warrants the CEO's attention. But, if I was a recruiter, I'd put in the same effort great CEOs put into making their key hires, into every hire I was responsible for. 

Where am I in the process?

Not surprisingly, I haven't heard from the recruiter and probably won't reach back out. I guess we all lose.

What do you all think?

Great Product Managers Steal - The Hardest Easy Job in Tech

We've all heard the (wrongly?) Picasso-attributed quote, "Good artists copy; great artists steal." And there is a similar quote around coding circles, "Great developers are lazy." However, this refers to the common practice of reusing code that someone else has already written. Well, the same holds true for product managers.

Now, before the trolls gather, I want to explain. I do not condone the use of wget as a tool of the trade. However, I do believe that imitation is the sincerest form of flattery. Also, inspiration is often derived from the collective conscious; that great site you used to do X, seeped into your latest instantiation of the feature you're working on. Which is to say, others can also be inspired, by the same things you were, to draw the same conclusion that you did. But, not all stealing is equal. So, now that that's out of the way, here's how I steal.

Product managers are problem solvers and lucky for us, if you have a wide enough lens, there are very few new problems. For example, MapReduce looks like something implemented in the Linux Kernel, which looks like a classic queuing problem. Now, this is easier said then done. As a product manager you are constantly looking to competitors, best of breed companies, and hockey-sticking startups to try to determine how you can bring some of that to your product / company. And if you aren't, it certainly doesn't help that your 'business counterparts' are. But, does implementing a me-too search engine make you Google. In actuality, it probably makes you more Cuil than cool. So, be careful where you steal from, because it might not work for your business.

Personally, I prefer to steal from as close to home as possible. Now, what does that mean? Currently, I work for Best Buy; a company in the middle of a great retail turnaround. Now, every analyst and pundit thought we were long-for dead; the nerdy kid who loses his lunch day after day to the elusive interwebz; a part of the new world of retail we just don't understand...

So, steal from close to home? You can't be at Best Buy long without hearing the story of Dick Schulze, our founder, and the company's entrepreneurial roots. And if you're lucky, you can find Dick on-campus and ask him about it yourself. The gist is retail is a simple business. When an entrepreneur worked in a single store everyday, he was able to deliver an experience that allowed him to build what you know today as Best Buy. As a product manager for Best Buy, that's where I choose to steal from. Dick's customers back then, are my customers now (more or less). The company culture from then, is the company culture now (more or less). Rather than trying to turn Best Buy into Amazon, I rather turn Best Buy into Best Buy, just a modern version of past glory days. In the current era, that means web, mobile web, apps, omni-channel experiences (where the web and the store meet), in-store analytics, complex algorithms and the like. But, we can't focus on new applications of new technology in an old space. We have to focus on customer problems, which tend to be old, core problems that are incrementally different because the world has changed. For example, customers have always wanted competitive prices and a great in-store experience. But, now, the bar is higher than it has ever been. And since everything old becomes new again, I prefer to look back and see what worked in the past and use it as the inspiration to go forward.

As product managers, we have to discover what delights and what solves actual customer problems and scale that to the world we live in today, with an eye on where we might be tomorrow.

Now that you've seen what makes it easy, let me introduce you to what makes it hard. The world has changed. The customer is more sophisticated than ever and is ever becoming harder and harder to impress. In most cases, the customer knows more about a particular item than an employee. If I want to buy a blue dinglehopper, 30 seconds of internet research makes me as, if not more, knowledgable than the sales person. And the advantage of being able to get something now, by going to a store, is quickly waning. After all, how many things do we actually need RIGHT NOW? And if you are Best Buy, it's really hard. Why? Because our solutions have to work for more than 100,000 Blue Shirts, in more than 1100 stores, selling hundreds of thousands to millions of products, to more than 250 million annual visitors.

So, when you steal, steal solutions to customers' problems and ALWAYS start with the biggest problem. Nothing hurts more when you deliver a product only to find out that Your Solution Is Not My Problem

What Sprouts Farmers Market Can Teach You About Social

In a world where everyone is offering some widget, gizmo or gimmick that promises to give you Facebook-like viral growth / visibility, I see a lot of social done wrong. While working for startups, I sought out these solutions to help 'get the word out' and in my current role, not a day goes by where someone doesn't try to sell me some social service that'll fix all our problems. So, I feel very comfortable saying that most of the market focuses on how to enable social sharing...in hopes that people will just share whatever content it's attached to. Now, how many of you have added sharing widgets to your website?  How did that work out for you?

Today was different. In the most unexpected of places, I had an experience that I'm going to share with you and, hopefully, you'll see why I was so excited to get home and blog about it.

After picking up my son, we stopped at Sprouts Farmers Market in Hemet, CA (It's where I live, don't judge me). Now, my son Joey has autism and April 2nd was World Autism Awareness Day. He was proudly sporting his newly acquired Build-A-Bear Autism Speaks Bear, just like he is in the picture below.

During checkout, I was reaching for my wallet, when Joey told our cashier Yesenia that this was his bear, he cleverly named it "Autism" and that he had autism.  She warmly smiled and commented that she liked his bear.  Then, Joey noticed  that Yesenia's name tag / lanyard had a blue puzzle piece pin on it, much like the one on his bears' t-shirt.  Now, for any of you that don't know, the blue puzzle piece is Autism Speaks's logo.  Honestly, I'm not exactly sure why, but, Joey got SUPER EXCITED.  Then, Yesenia told us how Sprouts supports Autism through Autism Speaks and how, during their recent fundraiser, there were puzzle pieces like the one she had all over the store.  To which Joey replied, "I can paint puzzle pieces all over the store too!" In all honesty, I think he took her explanation as permission and might have even asked her for paint to start drawing on the windows in the front of the store. She smiled and, cool as a cucumber, rolled with Joey, without batting an eye. And then it happened. Yesenia asked Joey if he wanted her pin.  I'm not even sure she finished her offer before Joey said sure. At this point, I was in tears. Then, after almost handing it to him, she realized it was probably better to give it to me, which was very thoughtful.  Especially since she pretended not to notice me crying. 

As a parent of a child on the spectrum, you never know what your child is going to do or say, especially in public. But, it's stop phasing you pretty early on. However, you remain VERY sensitive to how other people react to your child's quirky behaviors, especially when you are in a public place, late in the day, when the meds are clearly wearing off. Oftentimes, people react poorly and the only saving grace is that despite the lack of sensitivity, understanding and patience in the world, your child really doesn't understand how terrible the people interacting with them are treating them. Needless to say, Yesenia small act of kindness was an example exactly what to do and I was very impressed.

Instantly, I wanted to take out my phone blow up my Facebook stream, letting everyone know what happened...but what one-liner would do this story justice?  So, I came home, snapped some photos on my phone, sent them to my email account and wrote a blog post.  Seems like a lot of effort, but well worth it for this moment. 

As a former Disney intern, I know Disney spend tons of resources drilling this type of customer service into their cast members, under the guise of creating "magic" and they are world-class at it. But, I wasn't at Disney. I was at the grocery store, with my son, in tears, because Yesenia decided she wanted to do something special to make Joey's day and create an experience that this parent and grocery-purchasing customer will never forget. And now I'm sharing this story, on their behalf, because I was so moved that I want everyone to know about what happened to me today and who was responsible for the experience. And that's the key.

The key to social is moving people so much that they feel compelled to share the experience with anyone that'll listen.  Whether it's something funny / clever, emotionally meaningful, visually stunning or cat-related, there are many ways to move people. Social isn't about a button or widget; it's about creating moments worth sharing.

They did, so I did. 

The Magic Words of Early-Stage Startups

There is nothing like putting your product out there for the first time, especially if it's your first product. Whether it's good or bad is irrelevant. As a entrepreneur, especially a first-timer, you're convinced you are on the cusp of changing the world.  That's how I felt when I started the now defunct Browsemob, (God rest its soul). The whole world was going to name-their-own price, while shopping on any e-commerce website, using our bookmarklet tool.  And who knows, someday the world still might.

I sent hundreds of emails, hit up events / conferences, cold called and sometimes just showed up to try to convince potential investors, potential advisors, potential clients...basically, anyone I could get a hold of that could possibly further the cause, that Browsemob was the future and this was their chance to be a part of it.  It was a truly magical time, filled with ups and downs.

Honestly, most people ignore you, grin fuck or never reply.  But, the experience taught me the magic words of early startups, which I'll share with you.  Whether you are talking to a potential investor, advisor, customer, employee (paid or unpaid), co-founder, random person you bump into at a bar, whomever...when you hear them, you know you've reach the optimal outcome.

Now, before I tell you what they are, I feel obliged to tell you that you have to have a refined, coherent spiel, which only comes with practice. Also, when pitching your product, you can't lead with an obvious ask for the magic words, otherwise they won't come or they will come, but it'll be disingenuous.  And now, the words..."What can I do to help?"

Those six words mean that you have done your job pitching an idea, that's not quite a business yet, but one day could be.  It means you crossed the credibility threshold and have at least 1 shot at getting someone to do you some sort of kindness, based on whatever it is you've just shown them; for entrepreneurs the world over, they've led to first customers, round leaders, introductions to co-founders / early employees, high-profile advisors and so much more.

So, get out there and hustle.  And when you hear, "What can I do to help?" smile, think of me & don't screw up the ask :-)