Inside My Brain

Thoughts about startups, tech, marketing, and life

CATEGORY: Startups

The life of a startup founder – when little things are big deals

Head in Hands

Here’s a little story about how warped my brain is from entrepreneurship, the roller coaster ride that being a startup founder is, and how my idea of a “win” has drastically changed.

Over the last couple of months, I’ve been doing customer development for my startup, WinOptix. I’ve spoken to over 30 government contracting business development folks to learn about their problems with the BD process and pitch my concept to get feedback.

I learned so much about the government contracting industry and received a ton of great feedback.

And to my surprise, one of these interviewees (let’s call him Victor, not his real name) said that he would pay to have a tool like WinOptix built!

(Yes, I definitely got excited about this at the time, but that isn’t the situation I’m writing about in this post.)

I told Victor I would get back to him soon. I hadn’t even incorporated the company nor did I have the ability to build the product, so I had to get to work on both fronts before moving the potential engagement forward.

At the same time, I was setting up my new WinOptix email address with Google’s G Suite. I emailed Victor from that new account.

Usually I would set up email forwarding to my primary email address so I can manage everything from one account and not have to check multiple inboxes. Except I forgot to do so this time.

Of course, Victor emailed me to set up a time to chat about moving forward soon. And I didn’t receive the email until I checked my WinOptix account much later. UGH.

I replied with an apology. No response. I emailed him again. No response. And again. No response.

I was totally bummed out that I might have missed out on the first paying customer because of a stupid email setup mistake. This could have been huge for WinOptix, and I just banged my head on the wall about how dumb I was and how I screwed up a massive opportunity.

I couldn’t stop thinking about my screw up and how I might have missed out on my first customer. I actually had some trouble sleeping and was down on myself for a while.

After a couple of weeks, I made a last-ditch effort and gave Victor a call.

To my surprise, he picked up the phone! He said he saw my emails and was planning to respond, but had been so swamped that he didn’t have time. And he said he was still interested in working together on the product, and will reach out soon.

I was ecstatic, just because of a simple phone call.

I didn’t even get a firm commitment, but the simple fact that the potential deal was still alive and that I didn’t totally screw it up was a big win to me.

I thought about how this situation – an email setup snafu, a missed email, then the redeeming phone call – is such a small, insignificant blip in the big picture.

But the impact that it had on me was profound.

Then I thought about a couple of things:

  1. Is this relatively small situation having such a major impact on my psyche a good thing for me?
  2. Is my reaction to this situation a telling sign of my ability to be an entrepreneur? Do I need to be more even keeled and steady, and not get so high when good things happen and so low when bad things happen?
  3. Do other early-stage entrepreneurs feel the same way?
  4. What does this situation say about my attention to detail?
  5. If I worked for a larger corporation, what would be an analogous situation, and would I feel the same way?

I’ll write more about these thoughts in future posts. To be continued…

What do you think about this situation? Did I overreact? Have you been through something like this – where a small situation has a profound impact on you? I’d love to hear your thoughts.

Photo courtesy of Alex Proimos on Flickr

When patience and perseverance can be bad traits to have

Patience and perseverance are excellent traits to have. But in certain situations, you don’t want to wait too long, or endure for too much time.

I wrote a post a while ago about how raising a kid is like running a startup, and I find that patience and perseverance can apply to both as well.

Being patient with your child is a virtue.

There will be times where your kid throws tantrums and just does things that she shouldn’t be doing. Over and over and over again. Or if you’re sleep training your kid and she just cries and cries and cries and sounds like she may never go to sleep.

And you might lose your cool.

Being patient, persevering, and teaching your child the right thing to do – over and over and over again – will make her better understand right from wrong. And letting her cry herself to sleep, even though it might be painful to hear, will be better for everyone in the long run.

Patience can help your startup and business succeed as well. Software-as-a-Service (SaaS) investor and expert Jason Lemkin says it typically takes 7+ years to truly build a SaaS company. And many founders give up too soon.

It takes some time to learn what you need to learn and do the things you need to do in order to be successful. At least that’s what I keep telling myself.

But when might too much patience and perseverance be a bad thing?

In the sleep training example, maybe your kid is crying for a different reason other than just not being soothed to sleep. She may have poo’d or pee’d, maybe you forgot to give her favorite sleeping toy to her, or it might be too cold in the room. If too much time has passed and she still isn’t sleeping, you should probably go in and check on her.

In the startup world, you have to realize when it’s time to jump ship. You might recognize that the founding team isn’t right for you, and it makes sense to split up. Maybe you see that no one really needs or wants your product, and it’s time to pivot to another idea.

In these cases, you might be wasting your time pursuing things that just aren’t going to work, and the best solution is to not persevere and just move on.

Overall, patience and perseverance are great characteristics to have. But the tough part is recognizing when they are detrimental to your particular situation.

The uncertainty of launching a startup product

compass

When you’re building a product for your very early stage startup, there will always be uncertainty. The weird thing is that it can come in different forms.

I’ve been part of building two startup products, even though they didn’t get very far. One was a smart calendar called Dokkit and the other is ribl. In both cases, I could envision exactly what the product would look like from the jump.

The uncertainty in Dokkit came when our team couldn’t quite agree on the product vision after building the alpha version. Everyone had their own ideas. We didn’t talk to enough potential users and didn’t validate what we needed to build. The end of Dokkit came shortly after that.

With ribl, the uncertainty reared its ugly head when trying to acquire customers after product launch. Again, we didn’t do enough to validate the concept, primarily because we had such a clear vision of the product and we were absolutely enamored with the idea. Big mistake.

Now I’m working on WinOptix and have spoken with a bunch of government contractors about their business development processes to thoroughly test the validity of the concept before building anything.

And unlike Dokkit and ribl, the ambiguity now comes in the form of not knowing what to build.

I’m hearing some excellent feedback about the government contracting BD world and the multitude of problems that exist. And one of those problems aligns with my initial hypothesis of what WinOptix might do.

But are the other problems mentioned bigger issues for my potential users?

Have I truly validated anything?

When do I start building something?

And what the hell do I build?

All of this uncertainty is stressful. I might make the wrong choice and waste time and money building something no one wants. That’s a startup killer.

But it’s exciting, too, because I’m confident that there are problems to be solved here. It’s just a matter of finding out which one will have the most impact. And it’s just more interesting than any other problems I’ve faced in other jobs. :)

Uncertainty is inherent in startups, and it can come in all forms. But that’s the exciting part, and I can’t wait to find my way through it all.

3 types of communities that are crucial for a startup’s growth

Communities have been an enduring theme on my podcast and have been crucial to the growth of many of my guests’ businesses.

While I’ve taken a break from podcasting, I continue to listen to past episodes and learn from my guests, and it’s no doubt how important communities are to their success.

Being involved with or building a community can be an extremely valuable way to engage with people who may later turn into customers, partners, and friends.

No matter what stage your business is in – whether you’re just brainstorming ideas or in the millions of revenue – there will be communities that can help move you ahead.

Let’s see what these types of communities are and how they can help.

Startup communities blog image

Local startup and industry communities

The first community that is very important when you’re launching a company is the community of startup founders, entrepreneurs, and industry professionals in your city or neighborhood.

For instance, if you’re a web designer in Raleigh, NC working on a financial technology startup, you should be part of and contribute to communities that focus on web design, fintech, and the general tech startup scene.

Being part of a local startup ecosystem can be a very powerful thing on many levels.

First, you’ll have a bunch of like-minded people with whom you can learn from and share your issues and concerns while you all are building businesses.

Regardless of whether you’re a solopreneur or part of a team, it’s always good to have an outsider’s perspective and an alternative point of view to solve your problem.

There is so much to do and to learn, and helping each other through the thick and thin is a valuable experience.

Next, you may be able to leverage your local network in order to gain customers.

Many of these entrepreneurs and small businesses are looking for products and services that you offer, and having that existing relationship gives you a foot in the door to make a sale.

You certainly want to add value before you drop the sales pitch on others, and being known as someone who gives before she gets is a great thing for business.

Finally, being part of the local entrepreneurship ecosystem opens the doors to many other networks, whether they are local or abroad, or directly related to your business or not.

By expanding your network, you may be introduced to future investors, partners, customers, and many others who may be able to help your business on one way or another.

If you’re a designer in search of a marketer, someone from your local network just may have a contact who is looking for that opportunity.

If your startup is ramping up and you’re in search for investors, a local entrepreneur may know just the person looking to make a bet.

As you can see, being part of your local entrepreneurial ecosystem can be extremely beneficial. But of course, it’s important to give before you get.

Volunteer your time at Meetups you’re interested in, provide some services for free, and be supportive of others in the community. Be known as someone who gives to the community and you’ll eventually receive benefits in spades.

Local communities are frequently spoken about on my podcast.

In episode 10, I chatted with Ron Schmelzer, the CEO of TechBreakfast, which is the largest monthly morning tech Meetup in the nation. If you’re into the technology scene, TechBreakfast events are great places to meet people like you.

In episode 14, Alec Hartman talked about how he is helping to grow New York’s tech scene by building TechDay.

In episode 16, founder Andrew Hyde and then CEO Marc Nager talked about how they launched and grew Startup Weekend to be a global phenomenon. Startup Weekend was one of the primary factors why I became an entrepreneur.

As you can see, there is no shortage of startup communities. No matter where you live, I’m sure that there will be a local startup or industry community waiting to welcome you, and being a part of these can pay off big time down the road.

Existing online communities

Existing online communities are the digital equivalent of your local community. The fundamentals of how they work are essentially the same, with the activity occurring on your laptop or mobile phone instead of in person.

Online communities will allow you to ask questions and garner answers from experts, provide your opinion and expertise to help others, make connections you wouldn’t have made otherwise, and potentially gain new customers.

But just like in local communities, you have to make sure to give before you receive. Blatantly promoting your wares won’t work, and doing so may get you banished from some of these sites. So make sure that you add value before extracting it from these online communities.

There are many community sites where you can interact with other like-minded people.

Reddit is the first to come to mind.

Reddit

There are hundreds of thousands of “subreddits” (topic-based forums on Reddit), where people gather to share articles and discuss and debate different subjects.

Going back to that example of a web designer in Raleigh, NC working on a financial technology startup, you can join the r/web_design (153,000+ subscribers), r/startups, (109k+), r/fintech (1k+), and even r/raleigh (10K+) subreddits to have a huge built-in audience to engage with immediately.

For more info on how to market on Reddit, check out this post.

Facebook Groups are amazing resources as well.

When I started my podcast, I joined podcasting Facebook Groups like Podcasters’ Hangout and Podcast Community. I interacted with hundreds of fellow podcasters each day, learned from them, and picked up a bunch of listeners and reviews.

Quora is another great community in which to engage. Quora is the best question-and-answer site on the web, and many smart people ask and answer questions that span all kinds of topics. You can search for and share your knowledge about thousands of different subjects. It’s a great place to both learn and teach.

Build your own community

One of the best ways to engage your customers for a long period of time is to build your own community.

No matter whether you build your community in the real world, online, or both, you’ll have a population of people who want to hear from and engage with your content and offerings.

Again, the keys here are to offer value, give before you get, and don’t always sell.

In episode 1, John Von Tetzchner, the founder of web browser companies Opera and Vivaldi, built passionate communities around these web browsers.

At Opera, Von Tetzchner built the MyOpera community to a scale of 35 million visitors per month at its height. The users frequently gave feedback on the product, and many volunteers contributed their time to testing unfinished products.

At Vivaldi, John was able to build a community from many Opera users who shared the sentiment he did – that Opera was becoming more of a commodity browser and he believed that browser users needed something more powerful.

So he developed online forums that potential users could join to talk about what they wanted from a new browser. The company engaged this community and frequently asked them for feedback as they developed the new browser, which gave the community a sense of empowerment and connection.

In episode 12, Luis Congdon talked about how his private Facebook Group has helped him grow his podcasting audience and sell a lot of his product, a podcasting launch course called The Podcaster’s Secret Weapon.

I am a member of Luis’ Facebook group and I must say that he does a great job engaging and providing lots of value to his audience without being overt about selling his products. And even when he does push his products, he does it in such a way that helps his constituents.

Conclusion

As you can see, communities are critical to the growth of businesses.

Regardless of whether you’re just at the idea stage, in the process of building your product, or have sold millions in revenue, being part of or building a community can help you engage potential or current customers and partners and set yourself up for success.

What are some ways you’ve leveraged communities to move your business forward? I’d love to hear from you in the comments.

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Thanks for reading!

Are you patient enough?

I was going through the airport security checkpoint this morning and the man in front of me (I’ll call him “Dude”) looked really impatient.

The guy in front of him (I’ll call him “Guy”) wasn’t even moving that slowly. He was doing the typical things – taking off his shoes, putting his luggage on the conveyor, etc. – at a normal pace.

Dude was rolling his eyes, trying to move in front of Guy, and just being kind of pissy.

We walked through the metal detector and gathered our belongings. Dude was rushing and walked off while I grabbed my stuff.

When I looked up, I saw that Dude left his suitcase on the conveyor. I called to him and he had to walk back to grab his bag.

His impatience made him forget something really important and necessary.

(I thought about the fact that he might be late for his flight, but I found out he was on my flight, which wasn’t taking off for a while.)

This can happen to anyone. We’re all busy and have places to go, and we want to get there as fast as possible.

I admit I’ve been impatient when it comes to the startups I’ve been working on.

In the startup world, you’re supposed to “move fast and break things.”

You’re supposed to “fail fast”, “hire fast and fire fast”, talk fast, run fast, blah blah blah.

And I get impatient when progress isn’t made each and every day.

Maybe I need to better understand that things take time to develop.

For my first startup, I was impatient when things weren’t progressing. It failed for a number of reasons, but I think one of them was due to my impatience of things not moving fast enough. And I left some relationships behind.

I think moving fast is very important. In an ideal world, you’ll make quick decisions, build quickly, iterate, learn faster, and move forward.

But sometimes you need to understand that things take time, and some of the best products and companies take years and years to find success.

If you move too fast, you might leave things behind.

Have you ever left something behind because you were too impatient? Talk to me in the comments!

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The importance of understanding your weaknesses – Chris Sacca on TWIST

Chris Sacca and Matt Mazzeo

Chris Sacca and Matt Mazzeo on TWIST — Photo courtesy of TWIST

I recently listened to part 1 of an interview with Chris Sacca and Matt Mazzeo of Lowercase Capital on This Week in Startups.

If you’re not aware, Lowercase Capital is one of the most successful seed stage investment firms in existence. Chris and Matt have invested in companies like Twitter, Uber, Stripe, Kickstarter, and many, many more.

The interview was really insightful and interesting. One of the things that stood out to me was when Chris said that he passed on Snapchat because he thought it was only about dick pics. When he told Matt that he passed, Matt was livid because he was a Snapchat user and thought it was an amazing product.

Chris is a little older, has a family, and thus has never swiped right or left (i.e. never used Tinder).

He isn’t in tune with the new ways that people are interacting with apps and each other.

This made Chris realize that his strength isn’t in taking the first meeting with a startup. He doesn’t “get” many of the products that are targeted toward millennials and younger people, so he’s not a good judge of whether he should invest in them.

Thus, he relies on Matt to judge those potential investments.

I love how one of the most successful investors in the world can openly admit his weaknesses and even more importantly, bring in people who can complement those shortcomings.

I think many times ego gets in the way and entrepreneurs (or anyone, really) think they can do it all.

Continuing to learn and understand new concepts is powerful, but sometimes you just have to realize that you can’t improve certain weaknesses enough. So you need to bring in additional resources and share the responsibility.

If one of the most successful investors in the world can be introspective enough to identify his weaknesses, everyone can.

It’s a powerful thing.

Have you identified your weaknesses, and if so, how have you dealt with them? Talk to me in the comments!

I hope you found this interesting! If so, please share this article with the share buttons on the left! That’d be awesome of you.

How important is alma mater when assessing job candidates?

graduation cap

Over the weekend, my buddies and I had a conversation about how much it matters where a candidate attended college when he or she is applying for a job. The context was that if I were to review a stack of resumes, how powerful of a signal is their alma mater?

One of my friends said that the university attended is a strong differentiator. He works in the pharmaceutical industry, and his argument is that many of the candidates have worked for other strong pharmaceutical companies, and that work experience is essentially equivalent. Thus, the college degree from a place like Stanford will trump the one from Rutgers. (Sorry, Rutgers.)

The other friend, who works in advertising and creative, argued that work experience trumps all, and that this experience will almost never be equivalent across candidates. Where the candidate went to college carries very little weight, and the companies where the person worked prior and the quality of work that he or she produced is a much stronger signal that can be defined.

I agree with both of them, because both situations are so different.

In the first scenario, I think where the candidate went to college is more important in science, technology, engineering and math (STEM) disciplines. These “hard” subjects are more clear-cut and objective, and the differences in formal training and education can be vast from college to college.

Also, it may be more difficult to differentiate the work each candidate has done in prior pharmaceutical and other scientific companies. Many times the work contains research that may not come to fruition or management of drugs that have been around for decades, so the impact of a single candidate can’t be determined accurately.

In the other scenario, I love the fact that employment can be based solely on the quality of worked that is produced – a pure meritocracy – and pedigree is a much less influential factor. A job really comes down to how you perform, so why shouldn’t your selection be based solely on your performance in prior jobs?

I do think this may be a bit easier to execute in “softer,” more creative jobs, those where you can actually produce an end product. If you’re a graphic or web designer, you can have a portfolio to display your work. If you’re an advertiser, you may have ad campaigns that you’ve worked on that can be seen, heard, and assessed, even if that assessment may be subjective.

Startups align more with the second scenario; if you are a co-founder, your success is judged solely by the performance of your company.

On the other hand, I think that some venture capitalists will look at the founders’ pedigree as a strong signal of whether to fund the company or not. A software engineer from Stanford or MIT may be more likely to be funded than a business major from the University of Central Florida. (Sorry, UCF.)

I can certainly see both sides. I have degrees from Lehigh, Georgia Tech, and NYU; nothing elite, but very respectable schools. So I can probably get by on my pedigree in certain situations, but chose the route where merit rules.

I just hope that I don’t ever have to apply for a job again. :)

Regardless, like many other things, the value of an alma mater comes down to the specific situation.

How important is alma mater when you’re assessing who to hire? And how important has your alma mater been in your career?

Tell me about it in the comments!

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How does other people’s success make you feel?

Unless you’re Bill Gates, Warren Buffett, or some other ridiculously wealthy person, there is always going to be someone who is more successful than you are, at least financially.

How does that make you feel?

I think other people’s success can bring out a spectrum of feelings.

Starting from the crappy end, you can be jealous and hateful.

You can complain that the 1%-ers get preferential treatment, claim that these people were raised with a silver spoon in their mouths, and say that they don’t deserve what they have. You can spew hate on social media or any other channel. That’s pure negativity.

Moving up the spectrum one step, you can be envious.

You don’t have what other successful people have, but you want it. There is definitely less outward hating going on, but inside you stew a little bit that others are further along than you are.

Next on the scale is indifference. Maybe you don’t really care about other people’s success and you’re cool with your current situation.

Finally, there is inspiration. Seeing others’ success motivates you to work harder, continue to learn, and achieve more. Witnessing how others have found their path in life makes you believe you can do the same and attain those levels of happiness, wealth, and satisfaction.

It doesn’t always have to be about the money, either. Success can be defined by your personal and social life, fitness and health, career, or some combination of those and other factors.

For me, in terms of my personal life, I’m indifferent and content. I have an amazing family, great friends, and a beautiful home in a great city. I’m healthy and happy.

Regarding my career, I feel a mixture of envy and inspiration.

I can’t help but be envious of other people’s career success, primarily because I haven’t quite found where I want to be and thus I haven’t gotten there yet. I haven’t made the impact that I’d like to as an entrepreneur, so I’m naturally envious of those who have.

But I do think it’s a healthy envy that inspires me to work harder, get smarter, and keep grinding. I want what others have, and I’m not talking about money. I want to launch and grow a company and have a positive impact on people’s lives, like many other entrepreneurs have done.

So how does other people’s success make you feel?

I’d love to hear from you. Write your thoughts in the comments, tweet at me @mikewchan, or email me at mike@mikewchan.com.

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Then sign up for my email list below and connect with me on Twitter for future updates. And check out my podcast at GoandGrowPodcast.com!

Do you have a Plan B?

Plan B

For the most part, it’s great to have a backup plan.

When an NFL quarterback is about to run a play but sees that the defense’s setup will defend it well, he calls an audible. That’s his plan B.

If you’re applying for colleges, you don’t only apply to one school, you apply to a few of them. If you don’t get into your top choices, your safety school is your Plan B.

In those cases, it’s great to have a Plan B. It may help you minimize uncertainty and adapt to certain circumstances.

But are there times where a Plan B is detrimental? Maybe.

If you know you have a Plan B to fall back on, you might not work that hard to execute and accomplish Plan A.

Take a startup for instance. If you have a backup plan, you might not focus on your current startup idea to the fullest. Or if you’ve raised a large round of funding, you may not efficiently spend your money knowing that you have so much in the bank.

Or if you’re a very wealthy individual, you might have your future spouse sign a prenup. When things get tough, you might not try as hard to work through your problems if you know you won’t lose half of your wealth if you split up. Total speculation here, by the way.

There actually has been a study done on this, where researchers determined that merely thinking about a Plan B may diminish the probability of success of Plan A.

It’s an interesting dilemma.

On one hand, thinking of a backup plan makes total sense, as you’d like to be prepared for anything that comes your way.

On the other hand, doing so might be detrimental to your success.

What are your thoughts on devising a Plan B? Do you know of cases where a Plan B was counterproductive?

I’d love to hear from you. Write your thoughts in the comments, tweet at me @mikewchan, or email me at mike@mikewchan.com.

I hope you found this interesting! If so, please share this article with the share buttons on the left.

Then sign up for my email list below and connect with me on Twitter for future updates. And check out my podcast at GoandGrowPodcast.com!

The power of healthy conflict

Maybe I should have been a trial lawyer, because I really like arguing. My wife and friends will attest to this.

I’ve had fierce arguments with my friends about why the US should move to the metric system (1s, 10s, 100s, and 1000s are much easier to work with than 12s), why people are wrong to hate LeBron James (he really only made one mistake in his career), and why the Common Core, while confusing and extremely different than how I learned when I was young, is actually a logical approach (because it focuses on frameworks and not rote memorization).

Fascinating, huh? :)

Anyway, the point is that I think conflict, as long as it’s healthy, and discussion, as long as it’s logical, are great things.

The ability to state your points, back them up with data, experience, and insight, and listen to other people’s different points of view can be extremely helpful and educational in both life and business.

I love how Silicon Valley venture capital firm Andreessen Horowitz allows for healthy conflict. Co-founder Marc Andreessen explained the process on his interview on the Tim Ferriss Show.

When someone in the firm brings in a potential investment deal, the A16Z team will absolutely skewer that person on every reason why that investment will fail. The person who sourced the deal will have to defend herself and provide reasons why the investment will pay off.

The best part is that even if the team doesn’t agree that the investment is sound, that person is still free to move ahead with the deal if she truly believes it will pay off, despite all the naysayers.

I think that’s amazing.

Allow discussion to occur and conflict to happen. If all of that feedback sways that person who sourced the deal, then so be it. If not, and she really believes in what she brought to the table, then she can move ahead and take responsibility.

The key point is that everyone needs to be rational and logical, and not emotional. Open minds have to be present to keep this conflict healthy so everyone can have a thoughtful discussion.

Healthy conflict can be a powerful thing.

How have you used healthy conflict? I’d love to hear from you. Write your thoughts in the comments, tweet at me @mikewchan, or email me at mike@mikewchan.com.

I hope you found this interesting! If so, please share this article with the share buttons on the left.

Then sign up for my email list below and connect with me on Twitter for future updates. And check out my podcast at GoandGrowPodcast.com!