Inside My Brain

Thoughts about startups, tech, marketing, and life

Alignment with Co-Founders – Lessons Learned From Past Startups Pt. 2

Last week I wrote about how aligning your idea with your current life situation, skills, and interests is really important.

This week, I’m going to talk about about how important it is to be aligned with your co-founders, which may be the most important aspect of your startup.

Man, have I learned some lessons here.

Mistakes with Dokkit – Getting Married Before Dating

My first startup was Dokkit, a smart calendar app where you can find your interests (e.g. the New York Yankees or the 9:30 Club) and easily download their event calendars to the calendar of your choice.

Dokkit didn’t get very far because the co-founding team wasn’t aligned at all.

This was completely my fault, because I recruited three engineers to join the team really quickly, and we didn’t take the time to feel each other out.

In essence, we got married before dating.

This led to a number of issues.

First, we had different work styles that didn’t mesh at all.

Next, all of the engineers had full-time jobs, while I was primarily working on Dokkit. So our schedules and time commitments didn’t align.

Finally, we just had different visions of what Dokkit could be.

It’s no wonder why Dokkit never got anywhere.

After Dokkit and Ribl

After we stopped working on Dokkit, I wanted to make sure that I had a strong relationship with anyone I might work with as a co-founder in the future.

My next co-founder would be Jeff Thorn, the CEO of Thorn Technologies, whom I worked with on ribl. I consulted for his company (and am now its CMO) for a couple of years before started ribl. So I knew that we worked well together, and we still do.

We launched and grew ribl, and it came and went. Oh well.

After we stopped working on ribl, we worked on deciding what our next startup project would be.

After almost a year of tossing around ideas, we couldn’t agree on anything.

Why not? I think this is where our alignment, or lack thereof, came into play.

I was more interested in products in the marketing and sales space, since that was where my expertise was strongest. He and the rest of the team were more interested in building tools for coders, since that is who they are.

I had a bigger appetite for risk. I could go a few months without a paycheck, while Jeff could not.

I wanted to move faster and dedicate more resources to launching a product. Jeff had a services business to run.

So while we’re still working together at Thorn Tech, we’re no longer working together on a startup.

Conclusion

Bottom line is that you gotta have alignment with your partners.

Do you work well together? Do you want the same things? Are you willing to sacrifice the same amount of time, money, and sanity? Are you on similar timelines?

If one of you wants to build a company that grows really fast while the other wants a lifestyle business, it ain’t gonna work.

If someone wants to sell the company within 5 years while the other wants to build a generational company, it ain’t gonna work.

If one wants to risk it all while the other is more conservative, it ain’t gonna work.

Founder alignment is so important. So don’t rush into getting married with a founder. Take the time to make sure you work well together and are aligned on most if not all of the aspects we discussed.

I’ve made multiple mistakes here. Learn from me and avoid these gaffes!

Have you had co-founder alignment issues like I have? I’d love to hear your story!

Lessons Learned from Past Startups – Alignment with Idea

 

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As I’ve worked on my startup WinOptix, I’ve thought a lot about the mistakes I’ve made in my past startups and how I can avoid making those errors again. So I figured I’d write a few (or many) blog posts about my lessons learned.

The first lesson I’ve learned has to do with how to select an idea or space that you’re properly aligned with.

The mistake – ribl

The first big mistake came on my second attempt at a startup, ribl.

ribl is a location-based messaging app, something like a localized Twitter. We were chasing the SoLoMo trend – Social, Local, Mobile – which should have been a red flag right off the bat.

For apps like these, network effects are super important. The more users you have, the more value your app provides. Think about social networks like Facebook or even the fax machine (if you’re old enough to know what that is). The more users on each platform, the more people you can interact with on the platform or with the tool.

In ribl’s case, the more users we have, the more content would be posted by these users, and the more value new users would get from interacting with this content. And so on and so forth.

So you really need to dedicate a lot of time to growing your user base very quickly to achieve these network effects.

But my co-founders and I were primarily working on growing Thorn Tech, a software development services agency, for our day jobs. Thus, we weren’t fully dedicated to ribl and couldn’t focus enough time to iterating the product and growing the user base.

Even though we built a great mobile application, the business model of ribl was just too dependent on the number of users. We wouldn’t have been able to monetize ribl (with advertising) until it had millions of users, and we couldn’t dedicate enough time nor move fast enough to feed that beast.

Essentially, the idea of ribl wasn’t aligned with our current situation and the amount of time we could dedicate to it.

Applying the lesson learned to WinOptix

After we decided to stop working on ribl, I realized that the next startup I worked on had to really be aligned with my life situation, interests, and expertise.

I’m still working with the guys at Thorn Tech on the agency but we aren’t pursuing a startup together anymore (more on this in a future post). So I’m still in a similar situation where my startup is a side gig, and I don’t have enough time to dedicate to growing a consumer application.

This definitely factored into the industries and products I would pursue and how I decided to work on WinOptix.

WinOptix is a platform for government contractors to make better sales decisions, so I’d be selling to businesses instead of trying to grow a massive consumer user base. I’ll still have to move fast and dedicate a lot of my time to growth, but it’s a much more measured, sales-based approach.

WinOptix also has a clear, revenue-focused business model. It’s a software-as-a-service (SaaS) application where future customers will pay a monthly or annual fee for the software.

So I can monetize with a single customer, as opposed to needing millions of users to start earning revenue.

While getting one customer will still be very tough, this situation is a much better fit with where I am in life. In addition to working on the startup part-time, I’m a bit older with a family, so the consumer app revenue model just doesn’t jive.

Also, the subject matter of WinOptix is more aligned with my strengths. WinOptix is a sales, business development, and analytics tool, three subjects that I’ve been intimate with for all of my career. And even though I haven’t worked in government contracting, I’ve been able to understand the industry and identify problems through over 40 customer development interviews with experts in the field.

Overall, WinOptix is a completely different business that fits my situation much better than ribl ever did.

Conclusion

The alignment of your idea with your life situation, interests, and expertise is extremely important.

I’m not saying that your idea needs to perfectly match all aspects of your life and career. If you find a problem that you’re super passionate about that doesn’t quite align but you think you can make it work, by all means get at it.

But I’ve made this mistake, and this lack of alignment was one of the primary reasons why ribl failed. If we had the foresight to see this misalignment, we may have been able to use that time and effort on a concept that fit us better.

The next time you’re thinking of an idea or space to pursue, consider the alignment of that idea with your current work and life situation.

What are your thoughts on alignment of the idea with your situation? I’d love to hear what you think in the comments.

Should you work on your weaknesses or focus on your strengths?

I recently listened to an episode of the podcast Seeking Wisdom where David Cancel and Dave Gerhardt from Drift talked about why you should forget about your weaknesses and focus on your strengths. Read the blog post here and listen/watch the video at the end after you finish reading this post. :)

This point of view certainly makes sense. It’s frickin hard to learn or get better at something that you’re not good at. And because it’s hard, you’ll also get frustrated when you make slow progress.

So maybe that time would be better spent on focusing on your strengths so you can turn them into superpowers, and delegating the stuff you’re not good at.

Here’s an excerpt from the episode’s blog post about one of David’s weaknesses:

For example: I’m not great at following up (especially with email). I’m a momentum maker. And that means I’m better at focusing on the here and now than I am at staying organized and creating process. But I used to fight it and I would focus on every single hack and trick to try and help — from to do lists on my laptop, reminders on my computer, phones on my phone, notebooks, etc.

This lesson took me a decade to learn. But eventually I learned the secret: I needed to double down on my strengths and surround myself (and team) with people who complement my weaknesses.

As a non-technical startup founder, it would be faster for me to recruit a technical co-founder or a contractor to help build the app. So instead of learning how to code, I could focus on customer development, marketing, and sales, all stuff that I’m much better at doing.

I do think there are situations where spending time on your weaknesses makes a lot of sense.

High-leverage activities

The first is if that weakness is a high-leverage activity that will have a substantial benefit if it’s improved.

In David’s example, being good at responding to email is a positive trait to have. But is it a high-leverage activity? Is it worth spending a decade trying to figure out how to get better at it? Or can David easily hire someone to help him respond to emails and be more organized?

On the other hand, for my situation, coding is a high-leverage activity that would benefit me greatly to know how to do.

Software developers are tough to recruit, but I was able to snag one on a contracting basis to help build WinOptix. Things are going great, but what if he decides to leave? I’d be shit out of luck.

And if we continue to work together, understanding how to code will allow me to 1) better estimate how long it will take him and others to build features of the product, and 2) contribute to the development of the product myself (eventually).

If your weakness is a high-leverage activity, it might make sense to put in the time to improve it.

If you don’t really like your strengths, enjoy working on your weakness, or both

Let’s say I’m strong at marketing. But one day I just get sick of writing blog posts, promoting them, running paid ads, and all of the other tasks that marketing entails. What should I do then?

The first thing I should do is assess my career. But what next? Should I continue working on my marketing skills, even though it kills me inside?

And let’s say I’m weak at programming (I am), but I looooooooove it (I don’t. It’s aight, but I don’t know enough to love it yet). Should I not try to improve my coding skills, just because I’m not really good at it?

Or what if both were happening at the same time?

Focusing on my strengths certainly wouldn’t make me any happier or necessarily better at my job.

Over to you

While I do see David’s point, there are certain situations where shoring up your weaknesses might make sense. I think the decision will be unique to each individual’s situation.

What’s your situation like? Are you focusing on your strengths, or working on your weaknesses? I’d love to hear from you.

BTW, David Cancel was an awesome guest on my podcast. Thanks David!

Successful products are either loved or needed. How about both?

Slack quote

Ted Leonsis has said that a successful product is either loved or needed.

Your electricity provider is needed.

Your Honda Civic or Toyota Corolla is needed.

Airlines are needed. They certainly aren’t loved right now.

Snapchat is loved but not needed.

Medium is loved. We didn’t really need another blogging platform, did we?

Tesla is loved; you really don’t have to spend that much money on a car to get you from point A to B.

The magic happens when your product is needed and loved.

Companies like Southwest, Slack, and T-Mobile have cracked that code.

Southwest has created a culture where they treat their customers well and make flying enjoyable.

Slack has built an amazing enterprise communications product that everyone is addicted to.

Even though its cell connectivity isn’t the best, T-Mobile just keeps coming up with ways to lure its competitors’ customers away and keep current customers around.

Even if your product is boring and unsexy, there are many ways that you can make it both needed and loved.

Add some personality to your microcopy. Make customer service central to your companyBe transparent.

There are plenty of ways to achieve both.

How are you making your products and services both needed and loved? I’d love to hear from you in the comments.

What kind of work gets you in the zone?

I have friends who just love to write, and when they start writing, they just get into the zone and can’t be stopped.

I’ve worked with designers who get into his or her flow, and the creativity just keeps pouring out.

There are people who just love to cook, and they can spend all day in the kitchen.

Amazing things happen when someone just gets so comfortable with and loves the work they do.

Some things come very natural to people, and they’re so good at their work and enjoy it so much that it almost becomes second nature.

I think that’s a beautiful thing.

Unfortunately, after 38 years on this earth, I don’t think I’ve found the kind of work that gets me into a flow state. My resume and career tells that story pretty clearly.

I’m a people person, so part of me thinks my ideal work would be in sales and marketing of some sort, not dissimilar to what I’m doing now. I thought I had a dream job working in marketing for a sports franchise, but that job ran its course, just like all the ones prior.

I’m also pretty analytical, which is why I gravitated toward engineering for my undergrad and grad degrees. And I’m learning Python, which I’m enjoying as well (though it’s hard as shit).

I also like to build things. And I like to write sometimes.

I’m a man of many interests. And that might be holding me back from finding my ideal work.

Who knows, maybe someday I’ll find the work that gets me into the zone. When I do, I’m sure it’ll be a beautiful thing, because it always is.

What about you? What kind of work gets you into the zone? Maybe it’s a specific aspect of your job. Or it might not be work at all; it can be a hobby that you can do all day.

Whatever it is, I’d love to hear about it.

How Chess and Business are Alike

chess board

Whenever we visit Vicky’s family in NJ, my nephew-in-law always asks me to play games, and sometimes we play chess.

This brings me back to the days when I used to play chess against my Mom when I was a kid. I remember enjoying it, but not so much when lost. :/

Anyway, the more I play chess, the more interesting the game becomes, and the more I draw parallels between the game and business.

First of all, if you don’t know how to play chess, you have to learn about all of the pieces and what they can and can’t do. There’s a lot to pick up in a short amount of time.

Then you have to have a strategy that translates to tactics. What’s your opening move strategy? How will you protect your King? Do you like to attack with your Queen early and often?

Of course, you have to understand your competition. What’s his or her strategy? Are they aggressive or defensive? How might they react to your moves?

Throughout the whole process, you have to be analytical. Scan the situation, manage your risk, analyze your options, and select the best one.

Similarly, if you’ve never run a business before, you have to learn about many subjects, and quickly. Depending on the company you’re building, you may have to pick up product development, marketing, sales, customer service, accounting, recruiting, legal, and so on.

Then you have to plot your strategy, tactics, and implementation plan. How will you go to market? What channels will you use to acquire customers? How will you recruit for the skills that you need?

Knowing your competition is very important. How do you differentiate from your competition? Is this differentiation sustainable?

And it’s imperative to be analytical in business as well. Even though creativity and other soft skills are important, you have to know your numbers inside and out. How much does it cost to acquire a customer, and how does that compare to their lifetime value? What’s your profit margin and growth? How can you drive more traffic to your website and increase conversion rates?

It’s no wonder that many successful executives were competitive chess players.

I recently bought a chess board so Vicky and I can play. We’ll eventually teach Maya how to play as well. Hopefully she’ll learn how to be analytical and strategic, discover the parallels between chess and business, and then grow up to be a successful executive. No pressure, though. :)

Don’t be enamored with the vehicle, but what makes it run – knowledge from Questlove

I recently listened to an interview with Questlove of The Roots on Alec Baldwin’s podcast, Here’s the Thing.

Questlove is an extremely thoughtful, introspective, and smart person who had a ton to say about history, dieting, and much more.

But one of the quotes he said that stood out to me was that he “wasn’t enamored with the vehicle, but what makes it run.” I’m kind of paraphrasing the quote because I’m too lazy to go through the interview again to find exactly what he said. Sorry about that.

Anyway, I think that quote is very powerful.

Don’t pay all of your attention to that big end goal. Rather, focus on each specific, smaller task that you’ll have to accomplish to reach that goal, and you’ll achieve it.

Let’s take entrepreneurship, for instance. If you’re a startup founder looking for that big exit but can’t stand the day-to-day grind, you’ll never make it. But if you work hard every day and continue to learn every way to best serve your customers, you’ll have a better chance to build a successful business.

If you’re raising a child, are you longing for the day your kid turns 18 so he or she can go off to college? Or are you enjoying as many moments together as you can?

Are you working toward that one day when you can retire, or trying to make the most of each day of work and enjoy the ride?

Many times the journey is more important than the destination. So don’t be so enamored with the vehicle, but what makes it run.

When little things become big deals – is this a good thing?

A couple of weeks ago I wrote a post about how little things become big deals when you’re a startup founder.

One of the questions that I thought about was whether this relatively small situation having such a major impact on my psyche is a good thing for me.

On one hand, it’s obviously not good at all.

There are a lot of “small” bad things that can happen that can stress out any startup founder or early employee. You might lose touch with a potential customer, like I almost did. Maybe you typed in a wrong number that made you spend a few hundred dollars more on advertising than you planned. Or maybe you inaccurately communicated something to your team that led to confusion about what tasks needed to be done.

These things can add up and really fuck with your mind if you don’t deal with them properly. The stress may lead to poor sleep, crappy work performance, and strained relationships.

Of course, that’s not good for you in the least.

On the other hand, if you put things into perspective, this stress can actually signify a good thing.

It could mean that you truly care about the job that you’re doing. Your reaction to these situations might show that you’re really passionate about your work and the mission you’re trying to accomplish. It might mean that you understand the big impact that these seemingly little things could have.

If you were buried in a large corporation, these little problems might sting a little, but in the long run, they’ll likely be a drop in the bucket and have minimal impact to the livelihood of the company. With layers upon layers in an org chart, these small issues can easily get buried and ignored with little consequence, so you might not care about them as much.

I’m not saying that a startup founder’s job is more important than any other corporate job; I’m saying that in the early stages in a company, little things have a much larger effect on the company.

So when these little things bother you, it can be a sign that you really care about what you’re doing, and are committed to making sure everything goes well for the good of the company.

And that’s a great thing.

Use the hate as fuel to get better

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Last Friday I posted a blog post titled “The life of a startup founder – when little things are big deals” on LinkedIn. 

The very first comment on that post was written by one of my connections who interviewed me for his podcast a while ago. This is what he wrote:

Mr. Chan – Given my 20+ years of experience working with the poorest of the poor and families on the Forbes 50 you are so self absorbed that you think every small detail is the end of the world. I experienced this directly with you in trying to work together. I learned just because I am loyal doesn’t mean everyone will be. Stop only thinking of Mr. Chan. However, my business experience did teach me one thing never put all your eggs in one basket. My money is on your competition !

The situation that led to this comment was a misunderstanding that happened a long time ago. I thought we came to an agreement and squashed it, but I guess not.

While I don’t agree with his comment (obviously) nor do I agree with him using a social network to air his grievances before speaking with me in private, he’s entitled to his opinion about me.

I’m not writing this blog post to disparage him. I have nothing against him. We had a really great interview and hope his podcast is doing well.

But I’ve been thinking a lot about that comment and it’s been motivating me ever since it was written.

You’re going to have some haters out there, whether you deserve to or not.

Maybe your personality doesn’t jive with others.

Maybe your work style is different than others.

Maybe you have to break some eggs to make an omelet, and it’s others’ eggs you have to break.

And when that hate comes at you, you can either crawl into a hole and feel sorry for yourself, or you can use it as fuel to get better and prove them wrong.

I don’t like it when someone comes at me like that. It doesn’t feel good. I’m an overall nice guy and I think most people like me, and I’d like it to stay that way. I know I didn’t do anything wrong in that situation, so I’m not going to let it bother me.

Rather, I’m going to use that animosity to motivate me to work harder, build faster, and get better.

If he wants to put his money on my competition, I’m going to work hard to make sure that he loses that bet.

So don’t let the haters get to you. Use their hate as fuel for your fire.

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