small dogs / big dogs

What it’s like having a kid

In addition to the obligatory book reading and research my wife made me do, every once in awhile during her pregnancy I would do some searches online for “what it’s like to have a kid” or “what to expect when first child arrives” and most of what I found was either written for a Mom or was more clinical in nature. I’m sure I missed some great article or book specifically written for Dads, but for what it’s worth, here’s what it was like to have a kid.

I was laying in bed reading a magazine and my wife walked in looking like she’s about to burst, holding a pee stick in her hand. All she said was, “Adam…” and I knew.

Fast forward 40 weeks later and we’re hurtling down Lake Shore Drive at 11:30 at night, my wife in the passenger seat in some serious discomfort as her contractions are coming on stronger and more rapidly. I was trying to maintain a sense of calm for her sake but my internal panic was probably evidenced by the gas pedal getting closer and closer to the floor. Just an hour earlier she was having some discomfort but it seemed under control. I even made her mac and cheese. Now it felt like I was going to need to pull over on the side of the road and deliver this baby Macgyver style before we were going to make it to the hospital.

Fortunately the baby didn’t pop out and we pulled up to the hospital door and waddled in. A front desk receptionist handed us a couple things to sign and a triage nurse was called to take us in to a room to run some initial tests. The nurse had my wife lay down to check things out and take a bunch of blood. While all this is going on her contractions were getting more intense so I tried playing the role of relaxer, hand holder, and smiler all at the same time. The problem was I’m a little squeamish when it comes to blood and hospitals in general. I’ve never been to the hospital other than to visit other people there, but this was no time to look away, stand in the corner, or ask to lay down! I just hoped I didn’t outwardly display my fear through too pasty a face.

Once the tests were over and the hospital agreed she was indeed in labor(!), we were checked in to a delivery room. The doctor on call came in to perform another assessment and monitors were connected to track the baby and Mom’s heart rate and other vitals. She was still in major pain from the contractions and I felt helpless seeing her that way. I knew there was nothing I could do to help except walk her through her breathing and massage exercises we had learned in birthing class and avoid the sarcastic comments I’m prone to make. 

My wife also chose at this point to have an epidural which is a strong numbing agent that works from the chest, down. This would minimize her pain but also tends to slow down contractions. We were clearly in for the long haul.

Once the epidural was given though, my wife’s demeanor changed considerably and we were both a little more calm. The huffing and puffing and groaning had ceased and her ability to speak coherently returned. We had debated the decision of receiving an epidural a great deal because some believe it’s not a “natural birth” if you get an epidural and I’d put us at a midrange granola level with our lives in general, but we decided that for us, for her, it was the right thing to do.

At 2am her contractions had indeed slowed enough that the baby’s arrival was no longer imminent and we tried to both get a little sleep in the hospital room. Realistically I probably got 30 minutes of sleep and instead nervously refreshed Hacker News, Reddit, and the New York Times looking for anything to pass the time. 

At about 7am our doctor arrived at the hospital and paid us a visit. We were fortunate enough that the Doctor we had been seeing all along for check ups was also on call that day. She told us everything was going pretty well but there was one thing she was a little concerned about: every time my wife had a contraction, the baby’s heart rate would slow down by about 50%. This was fairly common we were told, and something that just needed to continue to be monitored and addressed by trying to lay in different positions.

An hour later our doctor came in again and took some dilation measurements. No progress over the past few hours, and on top of that, an analysis of some amniotic fluid collected from my wife’s water “breaking” showed the baby had #2’d inside her and had in essence contaminated the path she was supposed to be coming out of soon. So now on top of the heart rate issue, we had another issue working against us. But again we were told this was pretty common and could be dealt with. 

After more monitoring, at 10am our third strike came. Fever. Earlier in the evening my wife was running a slight fever. Now her temperature seemed to be climbing precipitously fast at +1 degree per hour. This could be a signal of infection in both her and the baby. Our doctor’s demeanor changed from cheery and supportive to concerned. She strongly advised us that instead of delivering the baby vaginally we needed to consider a C-Section where they make an incision in her abdomen and take the baby out.

A C-Section? The entire pregnancy had gone so smoothly and now all of the sudden we were being presented with a major fork in the road: continue on the path we were on to deliver vaginally which we had read was the very best option for the baby, or have this C-Section. I thought about how prepared my wife likes to be for things, about the walls of ink on pages of to-do items she regularly keeps at home and how organized she is. And how now she was being presented with a major decision that we really hadn’t discussed as much as we probably should have.

At this moment I felt like I was putting my wife’s life and the life of our baby completely in the hands of someone else. We were wholly dependent on their experience, their medical training, their judgment, their general mood that morning! It felt much like it does when I get on an airplane and think, “I’m now in the pilot’s, and God’s hands!” 

Medically, however it didn’t seem like there was much up for discussion and we decided to give our doctor permission to do the operation. We told the doctor and nurses who were huddling on the other side of the room of our decision and suddenly everyone sprung to action. Multiple teams of nurses were called in along with additional doctors to help support the operation. I took a few steps back from the bed and became a helpless onlooker as my wife was prepped for surgery. This was all happening way too fast. Suddenly they were wheeling her out and in the commotion we hadn’t even had a chance to say anything to each other. I could only see her capped head and arms hanging off the sides of the bed and a team of nurses and doctors surrounding her as they rounded the corner leaving the room. I sprinted to the door and called to her in the hallway to catch her eye and silently waved.

And then she was gone.

The room where she was supposed to deliver the baby was suddenly empty except for me, my sister who had arrived that morning, and our doula. A nurse presented me with scrubs and I was told I would be going in to the surgery room in 5 minutes. I put on the scrubs and started to pace and tear up and take deep breaths. All I wanted was for my wife to be ok at this point and nothing more. 

I was escorted in to the surgery room and was greeted by over a dozen people working the room. It was much colder than the other room we had been in and I was told to sit behind a curtain where I couldn’t see any innards, just my wife’s face. She was trembling and told me she couldn’t feel much and we silently looked at each other as the doctors and nurses did the command and response cadence you regularly see on TV. 

Suddenly we hear our doctor call out “Baby delivered, 10:42am.” But there was no cry, no holding the baby, no sound at all other than a team of pediatricians whisking her out to an adjacent room. We were told to expect not to hear anything when she was extracted, but the silence was still awful to experience.

Within 30 seconds though, I was summoned to come in to the adjacent room to see our baby. I was flooded with relief as this obviously meant she was alive and kicking. And indeed, there she was. Our baby girl, stoically laying on her back on a warming table, eyes wide open and slowly kicking her legs and waving her arms. People say this is supposed to be the happiest moment of your life when your child is born. I was honestly too overwhelmed to think about that then. But now as I write this and get a knot in my throat thinking about how big her eyes were and how it seemed she was looking at me as if to simply say “Hi Daddy,” I think it was.

The nurses let me take some pictures of her then wrapped her up in a blanket and let me carry her back in to see her Mom who was still on the operating table. My elation and wonderment quickly changed back to concern as I saw how uncomfortable my wife was. She was shivering uncontrollably and said she felt a distinct pressure in her chest. I held up the baby so she could look at her hoping to calm her down. We both cried and said how beautiful she was. The nurses took the baby from me then to run some tests and I literally had to hold my wife’s arms down because they were shivering so uncontrollably - a side effect of the anesthesia she had been given. Saying I was still “worried” was an understatement, but I took solace in the tone of voices in the room - still calm and collected, even jovial. At those moments I think you look for any sign that things will be ok even though doctors are trained specifically not to lose their cool.

The team finally finished the surgery and we were moved to a recovery room. They brought our baby in and we were able to do “skin to skin” with the baby and even nursed successfully for the first time (ouch!)   

And now we were three.

I went out to the waiting room and got my sister and the doula so they could visit my wife and the new baby. Since we were only allowed to have 1-2 people in the recovery room, I stayed behind. I called my parents. I called my wife’s parents. I texted close friends. And then I just sat for awhile and stared at the ceiling. 

I realized even with a pregnant wife for the past 10 months I had still been obsessed and stressed about running a company by myself, with listening to music, with reading, with running and what I eat, with watching University of Illinois sports and the Bears. The “stuff” that is essentially me. Having a baby had been so abstract. Sure I had a Wife with a growing belly laying beside me every night, but it still all felt like it was in “the future.” And then there she was, staring up at me from that warming table. Just like that, I wasn’t about me anymore, I wasn’t just a husband, I was now about her. A father. My world and thought process immediately became about supporting her and being a good Dad. About just trying to do the best I can by her and not screw her up too bad. All the hopes and dreams I had for myself suddenly became entwined with hers. It’s become such a cliche these days in politics to say “we must do this for our children and grandchildren,” but at a local level, at my family nucleus level, those words have never rung more true. 

Afterall, I’ve got a family now.

p.s. I focused almost exclusively on myself, my wife, and our baby in this post but I would be remiss to not mention the incredible support we got from our friends and families, especially my sister who is even more squeamish about hospitals than I am but was a trooper the whole time, our doula who was a steadying hand throughout our entire experience, our doctor who did a wonderful job presenting us with facts and articulating things clearly and concisely, and perhaps most of all, the nurses at the hospital who were friendly and warm and caring. They truly are the foundation of any hospital. Oh and of course our dog who has taken it all in stride and has a new smell box at home to enjoy.

Defending Yourself by Taking Stock of What You Have

Many people have written about a level of depression or jealousy caused by Facebook, Twitter, and blogs. Evidently we all try to create a portrait of ourselves to the outside world that is as positive as possible. Go figure :)

I think some personality types are more susceptible to this form of depression than others. I know I am. I feel tinges of jealousy at times, or regret, or annoyance. And I think about the kind of stuff I post or write about and I’m guilty of doing the same thing. Perhaps not consciously, but almost as an ingrained behavior to not expose anyone to anything “messy” or “weak.” 

To explore this further, I did a little experiment the last 3 days and wrote down some feelings I’ve had I would never dream of “self reporting” on my various social outlets. Among the many:

• Isolation and loneliness in relation to my business;
• Hurt feelings about people who I thought were friends (or my own family) rarely or never proactively reaching out to me even though I have some huge life changes going on right now;
• Inadequacy about my body after reading a posting about someone just completing an 8 mile run;
• Annoyance of seeing vacation pictures of a place I won’t be going to any time soon;
• Hearing about yet another successful life hack that I know I don’t have the will power to try myself;
• Yet another instagram photo making someone else’s life look so fucking cool

And if I did write about them, it would be something like:

“Just saw X’s pictures of his trip to Fiji. Must be nice, I’ll never to be able to afford a fucking trip like that.”

Can you imagine seeing your FB wall filled with those kinds of brutal truths? I can’t.

But irregardless of whether I would post them, there was a time when these types of feelings could dominate me. Multiple days would go by where I would feel awful.

And inevitably anyone reading my 3-day list might think: “why doesn’t he get off his ass and just run?” or “stop being such a wussy and just deal with it.” But it doesn’t work that way. I might think the same thing about your secret list and have some ready advice for you. But this is who I am, for better or for worse. These are my insecurities and worries and problems however trivial anyone else may think they are.

In contrast, what a vast majority of us DO have in common are positive things in our lives we too easily take for granted. I believe those things can be a line of defense against the onslaught of everyone’s relentless positivity and cool! 

Another list I put together. My line of defense list.

• A wife who is many months pregnant about to deliver in to our lives a wonderful little girl
• A wife who has shown me a new side the past few months: a side that tells me that I’m lucky to have her as the mother of my child
• A pipeline of business and some current projects that I both find interesting and are actually improving things in the world
• High School kids I have made a connection with through a volunteer program that will be first in their family to go to college.  I got to have a very small part in making that happen
• An old house that creaks and moans but has character and protects us
• A sister who lives only blocks from me that I’m closer to than ever
• A tightening group of friends who give better than they receive
• A “Benjamin Button” dog who has beat cancer and seems to maintain puppy-dom even as she grows older.

Look at the magnitude of one list compared to the next. Even writing it out makes me sit a little taller and turn up the volume on the music I’m listening to. It’s bedrock. My baseline to always fall back on. I’m damn lucky to have it.

I suspect if our world of connected more often than not makes you feel kind of shitty, you could make your own line of defense list to fall back on.

You’ll never bring me down with your vacation photos and nike run posts you bastards! :)

p.s. Follow me on twitter and I promise to complain just as much as I celebrate!

Business people: Good guys vs. Bad guys

“You definitely want to talk to him, he’s a really good guy.”

I hear this regularly when I get a reference to talk to someone. Today was one such reference. I had a conversation with a very accomplished businessman who I was told was a “good guy.” He was a successful trader here in Chicago, then started his own company which went public, then left that and started a boutique consulting firm. It’s irrefutable he’s a very rich, successful person. 

But it wasn’t his accomplishments that impressed me after talking to him or the content of our conversation. It was this person’s style. Friendly, but to the point. Not condescending even though he was multitudes more accomplished in his business life than I am. He showed genuine interest in what I had to say and asked questions that clearly showed he was not just listening, but comprehending what I was talking about. He was conscious and respectful of my time. As far as I know he could go home each night and put out cigarettes directly on the kitchen table and yell at his kid to make him a turkey pot pie. But in his business dealings, he indeed seemed like a “good guy.”

Contrast this with multitudes of conversations I’ve had over the years with other business folk under similar contexts (a potential business relationship.) Judgmental. Manipulative. Subversive. Like one big eye roll. No one gets it except them. I doubt very many people would refer to them as “good guys.” 

Sometimes people who are actually good guys get confused for bad guys. But don’t confuse impatience for being an asshole. The “good guys” tend to get impatient and testy if they think you’re wasting their time. Depending how successful they are - not saying something of value in 10 seconds may be “wasting their time.” A successful but well respected CEO may be like this. 

Thinking about this made me compile some attributes I think make up being a “good guy.” Things I strive for as I get older and people come to me to ask for my opinion or advice. Results may vary.

• Try and comprehend, don’t just listen;
• Ask good questions;
• Don’t just complain or critique, offer up solutions too;
• Be as straightforward and transparent as possible;
• Don’t waste people’s time, this means saying “no” a lot vs. stringing people along;
• Be willing to do the “low hanging fruit” assist - if it takes less than 10 minutes, help a brother or sister out;
• Be complementary when it’s deserved. Our society seriously undervalues a pat on the back every once in awhile

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A shot of anything to get productive again

Without a pressing deadline, I find it difficult to maintain a consistent level of productivity. This leads to procrastination which leads to staying up late which leads to lack of sleep which leads to even less productivity. It’s a vicious cycle.  Here are some ways I’ve found to do a reboot to get on the path of productivity again, even if just to get through a couple tasks I absolutely need to get done:

Music
There is something about slipping on a pair of can headphones, blocking out everything around you, and using music to bring you back to a zone of productivity. Classical music or post rock like Explosions in the Sky tends to be my go to vs. anything with lyrics to maximize focus.

Do a House Chore
There is always something to be done around the house, whether it’s a few dishes to be washed, plants to be watered, or a few weeds to be pulled in the yard. This gets me out of the procrastination cycle and back on a path to doing something. 

Write an Email
I perpetually owe friends an update on life. Writing them keeps me in their good graces and also gets me doing something productive again.

Go for a Walk
Fresh air and a little exercise, enough said.

Review Company Pipeline or Forecasts
Fuck. Didn’t get back to someone when I should have. Cutting our yearly targets a little too close right now. Reviewing your money situation as a small company is always a kick in the ass to get productive again.

Design Something
Most of my day is spent responding to emails, reaching out to current or potential customers, or thinking about new features. When I design something it’s always first with pencil and paper. Bringing myself back in to a purely analog world tends to get me focused again.

If Everything Else Fails - Pomodoro

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Maintaining perspective: false hope vs. real hope

In running Inkling, one of the most important skills I’ve needed to work on is understanding the difference between real hope and false hope, and I still to this day struggle with it. 

I’ll share a couple stories to illustrate what I’m talking about:

A year ago we had pretty serious acquisition talks with a very wealthy individual who had just been bought out of his last company and was looking for his next big project. We were introduced by a common friend, had an introductory meeting, then proceeded to have a series of additional meetings. We even got so far as to start a Basecamp to collaborate on the direction our company would take once he acquired it and infused it with some of his own funds. Given the number of meetings we had, I was pretty confident a transaction was going to happen. I had begun to tell close friends what was going on. I was quietly recruiting a couple people to join the new team that was going to form any day now. 

I’m sure you can guess what happened next. Crickets. Emails ignored. His interest went from high to nil. I still to this day have not heard from him again. I had real expectations something was going to happen, but I realized later, it was a false hope. I didn’t manage my expectations, was overly optimistic, and it bit me in the ass. I’m sure I even lost a little credibility with a few people.

Similarly, we’ve worked with many large companies over the years. Some are still clients, other have gone away. But I can’t count the number of conversations I had at the beginning of these projects where the person hiring us thought this was going to “get big.” They’re paying for 500 seats now but there are 50,000 people in the company. “There’s a real chance this one could get really big,” I would tell Nate. More false hope. 

These kinds of scenarios have happened enough times that I think I’m finally wising up. I’ve even come up with a formula I like to follow when trying to decide how optimistic I should be about something:

Level of Hope = Probability of event occurring + Impact + Control I/We have over situation

So replaying the acquisition scenario for example should have been: 

Acquisition: (Probability - very low) + (Impact - high) + (Control - very low) = Low-ish hope levels

Instead I was irrationally hopeful because of the level of impact an acquisition would have on our lives. The other parts of the formula which should have been counter balances to the impact level were only small blips.

Over the years I’ve learned that understanding what level of hope you should have is fundamental to so many decisions you’ll make every day: budget planning, schedules, strategy, features. If you’re overly optimistic, over time you’ll start to lose people’s trust. If you’re overly pessimistic, you risk seriously damaging morale.

A balanced sense of hope will go a long way in people not only trusting you as a leader, but keeping yourself sane on this long journey of running a company.

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Avoiding Depression While Not Running a $1B Company

Instagram sells for $1B. Evernote is now valued at $1B. Pinterest at $1.5B. 3 month old companies coming out of YCombinator are getting investments based on $10M+ valuations. And today will be the Facebook IPO which will likely put a market cap on the company north of $100B. 

This is not a post about bubbles, it’s a post about maintaining perspective when you are no where close to being one of these companies and never will.

As the founder of a small company in Chicago who only took $17k from YCombinator 6 years ago (YC-W06) and now runs a classic “lifestyle” business that support myself and a small team from client revenues, I find myself wavering between being fairly satisfied with the state of my business life to mild depression and jealousy that I’m not in a situation to be cashing in myself. 

Regardless, I still have a lot of passion and belief in my business and won’t be leaving it any time soon. Our growth path has been slow and steady, not meteoric. In the face of an ever frothy investment and acquisition environment, the need for emotional discipline as a small business owner who will never be the next tech or investment community darling is critical.

Assuming many others are in this same position or will be in the coming months/years, here is what I’ve learned over time to keep myself optimistic and psychologically healthy (my wife would beg to differ :) 

Spend time with friends who are not in tech or startups
I didn’t realize how important this was until I actually made an effort to spend time with people who work in insurance, are lawyers, or work at non-profits. It’s refreshing to hear about someone else’s work life, realize that the latest .ly startup who claim they will be  ”changing the world” still has complete irrelevance to most people’s lives, and even finds my business interesting and exotic.

Read the newspaper
I read the Chicago Tribune, The New York Times, and numerous political blogs religiously every day for one simple reason. They give me perspective that beyond the screen, there is a messy world out there of happiness, scorn, betrayal, heartbreak, victory, life, and death that has absolutely nothing to do with technology.

Go for a lot of walks
I walk our dog at least once a day and often twice. Walks are a great way to clear your head and gain a sense of optimism by the time you get home. I mix up my walk between residential streets and streets filled with small businesses. Every day I walk by those businesses I see the owners toiling away: organizing shelves, working the fryer, wiping counters. I am even on speaking terms now with a few of them. Camaraderie. Those guys are in the same boat I am.

Go visit some of your customers in person
Surprise, surprise, even in your little business there are customers or users who care about your product and have spent time (and hopefully money) on it which means they have opinions about it. They can tell you what they like and don’t like, tell you how it’s benefited them in some way. You’re not doing this just to plan new features. Spending time with these people will make you feel relevant and needed which is critical to maintaining the drive to keep pushing forward.

Maintain a healthy relationship with parents
The great thing about parents is they’ve known you all your life. Hopefully they’re proud of you no matter what and they often have a knack for being able to put things in perspective and not let your head get too small or big. If parents aren’t around, maybe another family member can play the same role.

Keep a journal (not a blog)
So much of what we write these days is for others. We are constantly worried about how we are perceived, whether it’s a FB post, tweet, or blog post for our companies. A private journal is a place where you can be brutally honest with yourself and get everything out of your head. When I’ve been at more extreme points of depression, I’ve realized it’s because I’ve been obsessing over one or two things for more than a day. Writing it down in my own voice with my own insecurities included that I would never tell anyone else about is a huge release.

Find a therapist, life coach, or mentor
I can’t recommend this enough. You need someone in your life who has seen your situation a hundred times before and can share with you lessons learned. More importantly, you need to go through the process of knowing yourself and learning what your trigger points are for your full range of emotions: happy, depressed, lonely, fulfilled. If you don’t know yourself, you’ll never find the stability you need to carry yourself. And this person can’t be emotionally invested in you, like a husband or wife or close friend. They’re too biased to tell you what you may need to hear.

Appreciate your time more
Here’s when I feel best about my business life: when I take vacation whenever I want, when I take naps almost every day, when I go in to our office for half days, or when I look at my calendar and realize I have complete flexibility with my schedule. I answer to no one. Value this rarity immensely.

I hope these techniques are helpful to all the 10 or less employee, 500 sq ft office space (or home office), bootstrapping, revenue-based business founders. It would be great to have millions to buy lots of stuff, live more lavishly, even donate more. But if you constantly dwell on what you don’t have, your life is passing by far too quickly and that’s no one’s fault but your own. 

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Not setting expectations correctly ruins deals

This week I was frustratingly reminded of a customer service “must do” after I was blown off by two companies I was ready to do business with.

The first example was personal: we are thinking about finishing the attic of our house and I received a reference from someone for a contractor. I called them, they visited for 45 minutes and took measurements. I liked the guy and appreciated his honesty about the issues we were going to run in to. I clearly conveyed my interest in continuing to move the process forward and he agreed to get me a quote “by Monday or Tuesday at the latest.” It’s the end of the week and I still haven’t heard from him. In our very first meaningful interaction, he’s blown it.

The second example was with my business. Great meeting at the beginning of the week and it was clear we both wanted to move forward. I was promised an immediate follow up with this person’s business partner to begin working on the contract. Instead, there was silence. Now I’m nervous to do business with them because this may be indicative of how they treat their clients and they’ve planted a seed of doubt in my head they’ll have to work to overcome.

In people’s desire to meet expectations, they end up setting unrealistic expectations. Then they blow the deal. People just want honesty. Even if you know it’s not what the person wants to hear, it’s far better to tell them what’s possible than what’s fantasy. 

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