First vacation thoughts

I’m back in the office after a few days in Hawaii. It was Colin’s first plane ride and a fairly long one as well. Overall, he did great. The flight there was relatively seamless minus a blowout during the landing. He was a lot more fussy on the second flight which was a much fuller flight on a smaller plane. But all in all, he did great and adjusted to the two hour time zone difference fairly well.

I have heard a lot of parents say that a vacation with their kid(s) isn’t a true vacation. For better or worse, I experienced that for the first time. To begin with, it was a lot to prepare and pack for the flights. There’s no more traveling light with a kid and we are now the family with a push cart with a stroller bag, car seat bag, our luggage, and another bag for Colin.

Of course, the thrill of arriving for vacation never goes away and we were stoked to be there, and see my sister. But once there, we quickly confirmed that there just wasn’t a lot of time for ourselves. He’s still just a 4 month year old and requires a lot of feedings and regular naps. Our ability to do activities are always dependent on his schedule.

We had some nice pool and beach sessions, but they were short given his schedule. He did allow us to get some nice lunches and even a couple of dinners with my sister and her boyfriend so I am incredibly grateful for that. But there was not a lot of time to relax and enjoy the trip for ourselves. The result is that Sophia and I are just tired now and we’ll need a few days to get readjusted back home.

On the positive front, it was a magical thing being able to take Colin to the beach and pool and take him into the water for the first time. He was also able to bond with my sister and her boyfriend quite a bit. Watching him hang out and smile on the beach was all worth it in the end.

The new reality of life will take some getting used to and I need to give myself a bit more grace. All in all, it was a special memory I’ll have for life and we’re fortunate to have been able to take this trip. Fatherhood has been a net positive in my life and despite being tired, I would’ve done it again to be able to have that experience with Colin.

Aloha

It’s my last day before taking off for Hawaii tomorrow. We’ll be taking him to Oahu to see my sister and hopefully get some R&R before Sophia goes back to work in a couple weeks.

It’ll be our first flight with Colin. I’m not really nervous anymore given that Colin has handled nearly everything like a champ. I’m sure there will be some minor issues, but he’s just been great in everything that we do with him.

However, I am getting anxiety with just how much shit we have to bring nowadays. I’m usually a very light packer and like to be nimble in my travels. I’ve now got a checklist for all the things that we need to bring like his pack and play, stroller, car seat, etc.

Of course, the last day before a vacation always seems to be hectic. After a chill Monday and Tuesday, I am now drowning in work and meetings. It wouldn’t be a vacation without me being absolutely swamped the day before I leave though.

It’ll all be worth it tomorrow once I have a bowl of poke in my hands. I’m excited that we get to spend time with my sister who I will unfortunately see a lot less now that we’re moving to New York. Having her in Oahu was always a nice perk and a great excuse to take the short flight from SF.

I’m also excited for my first of hopefully many trips with Colin. I hope we have a lot of travels in our lifetime. It’s one of my loves in life and I hope that Colin gets the opportunity to see the world as much as I’ve been fortunate to.

New Year Revamp

While the calendar year flipped 2 months ago, there’s just a ton of clean-up work after year-end. We need to finish performance reviews, close the books, and recap 2024. Then we need to finalize 2025 plans and initiatives. At the end of February, we’re finally ready to put 2024 behind us.

The new year is always a good time to build on what we did last year, but also revamp some our processes and strategies. When you’re in the heat of grinding, you can often forget that things get stale quickly. That pitch or deck you’ve used could’ve been made years ago and not adjusted for today’s day and age.

One simple thing that we’ve realized is that we haven’t done that great of a job getting out and meeting our clients in-person as much. With the advent of Zoom after COVID, things are just too convenient to do a Zoom call. However, we often lose that human touch. In 2025, we’re going to make it a point to get out and meet our clients in person more.

These small things can lead to big results so hopefully some of our initiatives that we’ve started in 2025 will pay off.

My own mortality

Colin is turning 16 weeks tomorrow which is crazy to think. It feels like every week his personality comes out more and more and it’s been fun watching him grow. I’m incredibly fortunate that my work allows me to be home and around him a lot. That wasn’t always the case for me in my previous jobs so I’m counting my blessings.

With a chill weekend that was spent mostly at home with Colin, I had a lot of time to catch up on life. For one reason or another, I also started thinking about my own mortality a lot this weekend. It wasn’t necessarily a bad thing and I wasn’t worried about anything in particular. I was just hoping that I would have as much time with Colin as I could in this life.

On one hand, I found it a bit weird that I kept thinking about when my time was going to come. However, on the other hand, I think dealing with the fact that I will eventually die and my time here is limited allows me to live my life better.

I turn 35 in a couple of weeks. My Mom was 37 when she passed away. I hope that I have much more time with Colin that my Mom did with me but there are no guarantees in life. Knowing that I want to have as many years with my kid(s) as possible, I need to make sure to do my best to take care of myself.

Fatherhood and work

Friday couldn’t have come sooner this week. With the short week, just simply have not had much time to get caught up on anything. I’ve got a big block Friday after lunch to try to grind through my checklist and get into a good spot going into the weekend.

With a kid, I just simply do not have the hours in the day to catch-up on a lot of things anymore. My evenings are now strict times I need to be home to start taking care of Colin and then putting him to bed. There’s no more - “I’m going to have to work through the evening” type calls.

So far I’ve had to start my days a bit earlier now. I wake up at 5:30/6. Get ready, feed Colin at 7, and then pass him off to Sophia at 7:30 and head into the office. On most evenings, I need to be logged off and on my way home by 5 or 5:30pm to take over.

Of course, spending time with Colin is top priority so I’m happy to do it, but I am increasingly having to find time elsewhere to catch-up. That’s Friday afternoons and the weekends unfortunately.

Learning from the negative

There is no business in the world that makes every person happy. Even the best organizations that focus on customer success will have their slip ups and mistakes, or just deal with an unruly customer.

We deal with a good amount of negative feedback here too at Secfi. In our analysis, most of the feedback is in response to being rejected by us for various reasons. Unfortunately we cannot provide funding to every person that applies and there is only a small subset of companies that would actually qualify.

All that said, it’s our job to correctly set expectations. Of course, that’s really hard to do in our world as it’s not black or white. Individuals often come to Secfi and do not really understand their equity or the potential value on it. Perhaps someone at the company got them excited about the prospects of their equity or they had a friend who went through an IPO and they expected the same.

The reality is that only a small percentage of companies will ever realize an exit event in which common stock gets paid out. That fact is something in which Secfi is often the bearer of bad news on as we reject an individual who is looking for cash on their shares.

I am by no means saying this is an unfair circumstance. It’s the world that we live in and we need to do better in our communication to clients. One of our initiatives this quarter is to overhaul our rejection system based on the feedback we’ve received. People want more detailed explanations on why they were rejected and we plan to do just that.

New York Offices

We’re searching for an office right now in New York and it’s been more difficult than we’d like. Our current space just doesn’t work for the team right now and they are also shutting down this summer.

We initially had thought that we wanted to move to another co-working space temporarily. This would give us time to figure out a longer term lease. And also give us flexibility to grow up or down as needed. I also had hoped to fix our call room issue with multiple smaller offices.

We quickly nixed this plan once we saw just how much a coworking room cost. The flexibility is nice, but getting a 10 person office would cost almost double just signing a lease. In addition, the lease terms weren’t all that much flexible compared to a permanent space.

So now we’re looking for 1-2 year leases in more permanent office space. That comes with it’s own downsides of course. We usually have to furnish the office and it also comes with additional costs such as electricity, cleaning, and building taxes. But at the end of the day, it’s a more economical solution for us.

We’re also now facing the debate of staying in the Flat Iron which is one of the most expensive and desirable areas or moving towards a more traditional office center such as FiDi or Midtown which is less desirable.

Lastly, we also face the debate of just how much this team will grow. We’re looking for spaces with 15, but we’re also worried that the space will quickly get crammed once we get to that magical 15 number and then we’re locked into a 2 year lease.

Ultimately, the only easy solution is to throw a lot of money at it which we won’t do. So we’re doing our best to be patient and smart in order to find the right space knowing there won’t be a perfect solution and there will be issues with nearly anything we choose.

The constant battle

At the beginning of each week, I like to sit down with a coffee and assess what we’re up against this week. I catch-up on critical things that I didn’t get to over the weekend. And then figure out what needs to be done this week.

Part of this is seeing our goals and where we stack up against that. Almost every week I always have a mild panic attack and my anxiety goes through the roof at this point. Constant goal setting is one of the tough parts of any demanding job, but it’s especially amplified at a small startup.

You set goals and work your ass off to hit them. And if you do well and hit them, the goals get bigger every month, quarter, year, etc. Adding to the fire is that in startup world, you could be a situation where your company dies if you don’t hit goals.

That is unnerving and at Secfi, we’re fortunate that we’re not in that position. But at the same time, the thought of hitting goals constantly does weigh on me quite a bit. Hence every Monday I have anxiety for a few hours until I can calm myself down throughout the day.

The reality is that running most businesses are always going to be stressful. You sink or swim by the revenue you bring in. If you don’t close deals or find work, your business will die. That’s why entrepreneurship is hard - there’s always that constant battle that never goes away. There will be good times and bad times, and things get especially tough in the bad times.

However, if it was easy then everyone would do it. Whenever I go through doubt and see these daunting tasks, I try to remind myself that I’m in this position for a reason and that people believe in me. I can actually do this job and do it well.

Afterall, I recall that at this time last year I was perhaps in the same exact position. We were at our management team meetings in St. Louis and had just set a daunting goal for the rest of the year. I told the team that this would be a stretch and if we got there, we’d have to work really hard and things would have to go our way. In other words, it would be a stretch goal and unlikely.

Well we closed out the year at 96% of that goal. We did work really hard, but the goal wasn’t as unlikely as we all thought it was initially. The number just seemed daunting. But it’s amazing what you can do if you put your mind to things. Whenever things seem scary and my anxiety starts crazy with these daunting tasks, I need to remind myself that I can do this job and I do it well.

Entitlement

I was disappointed all afternoon after learning about a situation with an ex-employee. I feel that I’ve always done my best to treat our employees with respect and look out for their best interests.

I am of the belief that good managers know that employees can leave, but great ones know that employees will leave. I understand that Secfi will not be the last job almost all of us have and that there will always come a time for people to move on. We’ve largely always been supportive of our employees going for opportunities out there and even starting their own businesses.

However, there’s a level of respect and dignity you need to also have as an employee. Most of it is common sense. And there’s a line you don’t cross. I was really disappointed to hear that someone not only crossed the line but probably went 10 steps further. It’s really a big shame that things like this happen and people have this sense of self-entitlement.

It is what it is though and we all need to move on. But it definitely left a sour taste in my mouth going into a nice long weekend.

The era of Slack

When I first started work, everyone had phones on their desk. We had instant messaging but often the messages were sent to say “call me”. It was fairly normal to call up a colleague to ask a question quickly. Nowadays, that is completely gone. It’s almost weird for me to randomly call a colleague without any context.

One thing I’ve realized recently is that I’ve done too much Slacking and I need to call people more. There’s too much that gets lost in translation via Slack messages. And often times, the best course of action is to speak live and communicate verbally to get shit done. As our team is across multiple time zones, I’ve resulted to Slack a lot more and it’s hurt our communication.

Secondly, my Slack messaging is probably too direct and harsh at times. I try not to mess around on Slack and go direct to the point, but perhaps I can go too far. In this day and age, texting and Slack just requires a different vibe than what was normal years ago. At fear of me becoming that old grumpy man on Slack, I’ll need to make changes.

Speed vs sanity

The beauty of working at a small firm is that you can just move a lot quicker on things you want to get done. There’s no red tape and approvals. Just get it done. The downside is that there’s never a shortage of things to get done.

For people that love to get shit done like myself, this can result in me sprinting through my to-dos and checklists as fast I can. It’s a bit of an addiction at times. You can see how this is a problem when that checklist always grows given the nature of working at startup.

Unfortunately, we’re human and most of us cannot sustain sprinting through our work lives for too long. That’s a great way to lead directly into burnout which is not good for the employee nor the employer.

This is always a constant battle for me. I often feel guilty if I’m not sprinting as hard as I can to make sure that the company is in the best shape possible. At the same time, I’ve dealt with bouts of burnout as recently as back in January.

Unfortunately there’s no real easy fix here. It’s going to come down to long-term life improvements for me. I’ve done a real good job taking a step back on weekends to actually get a break. But I do an awful job really stepping away during vacations as it’s hard for me to be away for too long.

I suppose I should start there and really try to limit my work on vacations. Perhaps not even bring my laptop at times.

Secondly, I need to really work on making sure that work doesn’t consume my mind when I’m not working. It’s all too easy for me to be thinking about work when I go to bed at night. It’s not healthy by any means.

Staying positive

I had a tough and down day yesterday where I was tired and groggy most of the day. Unfortunately that carried over into a bad night of sleep. Now I’m sitting here on a Tuesday morning very tired in my office very tired and running on a few hours of sleep.

In periods like this, it’s really easy to feel really negative about everything. Perhaps it’s a bit too easy for me. I’ve unfortunately been in a more negative headspace the last few days. I suspect most of it is driven by just simply being tired from life. But I’ve also been pushing really hard at work to start the year off right and there’s a ton of things happening personally as well.

In short, I’m feeling a bit overwhelmed right now. I need to remember that these times are always temporary and everything passes. I also need to stay positive in life. It’s been way too easy for me to spiral into negative thoughts lately. A lack of sleep and life pressures will do that to you, but it’s important for me to nip this in the bud before it carries over into my life too much.

Weekends as a Dad

I had an uneventful but nice weekend. We didn’t really do anything too exciting and I spent most of the time just taking care of my son. For better or worse, this is probably the new norm now as a father.

My weekend evenings are now spent mostly at home. We relax a bit in the late afternoon. Play with Colin and then put him to bed. Then perhaps have a couple glasses of wine with Sophia and order a nice delivery dinner.

The weekend afternoons are filled with parent errands and outdoor activities. We go to the stores to get groceries and things we need for the week. Then we try to get him outside as much as possible. We spent Saturday afternoon at Fort Funston on a gorgeous day and took Colin for a walk.

Lunches at restaurants are perhaps the only time Sophia and I get to eat out nowadays. I miss going out to dinner with all my friends though. We try to make up for it by having some nice lunches.

At this age, there’s just not that much to do with Colin besides take him around with us and play with him. Everyone keeps telling me to enjoy this point in time because they get a lot more difficult as they run around so I’m aiming to do just that.

My life is a lot more boring nowadays, but boring is good and I’m really enjoying my weekends as a Dad.

DEI

DEI has become the target of the new administration since taking office the last couple of weeks. Nearly every major tech company has eliminated their DEI programs. Of course there’s a lot of people for and against these initiatives.

My stance on the touchy subject is that DEI initiatives were implemented with the best of intentions but things just went too far over the last 5 years or so. At what I believe to be the core concept of DEI initiatives is that we should ensure that underprivileged individuals get a fair shot at jobs in order to address systematic racism.

The reality is that I’ve lived a privileged life. I was able to go to great university out of state in which my parents provided for. Maybe I didn’t have the resources as some of those that are very wealthy, but I consider myself lucky and privileged.

Unfortunately, that’s not the case for many Americans. Individuals may be born into more difficult situations and perhaps were not afforded the luxury of going to a great school. Some may have been able to attend some of the better schools through merit, but may have had to go to the junior college route and settled for a state school which gets overlooked. These individuals may be more than qualified for roles but just may not have been given the opportunity.

If that’s what DEI is addressing, I’m all for it. Give everyone an equal chance if they are qualified for the position and ensure that racism does not hinder individuals.

Unfortunately, I do believe that DEI initiatives went too far. The idea is to give everyone qualified an equal opportunity, not hire or promote individuals solely because they were of a certain race, orientation, etc. Quite frankly when things like that happen, you just stray into racism in a different form.

All that said, I believe this war on DEI once again has gone too far the other way. I’m in favor at eliminating some of these DEI initiatives, but the rhetoric from this administration going as far to blame a plane crash on DEI is just absurd. I hope we can get back to common sense approaches to address our issues in this country. For now though, we just have to buckle up.

Momentum

It’s still really early in the year, but momentum in the private markets seem to be picking up. Anecdotally, I’ve noticed a large uptick of buyers in the secondary markets. Presumably investors are looking to capitalize on the projected IPO window opening up in 2025.

It’s been a slow market the last 6 months of 2024 and volumes were trending downwards. January was slow as always every year as we everyone eases back into work from the holidays.

As we sit here in February, we’re finally seeing some positive momentum finally. It’s early and things can change quickly, but it gives me a lot of hope and optimism for the year ahead.

Otsukaresama

My meditation today was about the Japanese word Otsukaresama which loosely translates to “good job”. The Japanese use this phrase commonly in the workplace as a greeting or a goodbye to show appreciation for someone’s efforts. It’s a way to say, I see you working hard and I appreciate your hard work.

I loved hearing about this and I wish we had something similar in the U.S. Obviously, we can say the words, “good job” and “I appreciate your hard work” but we need something a bit more commonplace.

The workplace at Secfi can be really frustrating often. We work in a highly specialized field that is demanding. We’re also a small company that requires a lot out of our people. Like any workplace, we can great frustrated at our colleagues and what’s happening.

All that said, I’m incredibly lucky to have a great team. This job just isn’t worth it if you don’t like the people you’re doing it with, and I’m fortunate to say that I love my colleagues. They’re rock stars and they always come through for me. Learning about Otsukaresama is a good reminder that I need to tell them I appreciate them more often.

Staying fit in 2025

With a new kid and much less time than I had previously, I’m now faced with the decision on what to change in my lifestyle. There’s a lot of hard things to give up, but that’s necessary when you have a kid. You just can’t have it all unless you have an amazing support system or a ton of money to pay for help. Unfortunately Sophia and I don’t have either of those luxuries.

The easiest thing to weed out is my social life. I knew that would suffer. I would golf less and see my friends less. Dinners out just don’t happen anymore. That’s fine.

One area that I’m for sure trying to maintain is my health. Obviously that’s probably the most important thing besides the kid. I used to be someone who loved spending 1.5-2 hours at the gym. I’m not a workout junkie, but it was a time for me to catch up on reading and get a good workout in. Or go on a long run.

In order to make this work, I’ve had to cut my time working out significantly. So last night I spent a couple hours researching the Minimum Effective Dose workouts which in short is the minimum amount of working out twice a week to maintain and build muscle.

I’m excited for it as it brings in new exercises and forces me to really focus on getting a good workout in. I’m hoping to condense my workouts down to 45 minutes tops with 15 minutes for stretching/showering.

Change is always a good thing and I haven’t been this excited to actually work out in awhile.

A new morning person

Last year, if you told me that waking up at 6am every morning including weekends would be my life, I would probably have said that’s my nightmare. I’ve never been a morning person and I have always struggled to go to bed early. Of course, I had to be up that early multiple times a week, but I’d at least catch-up on the weekends.

Enter Colin and my life is now 6am wake-ups when I am lucky and he decides to sleep through the night. Prior to Colin, the anxiety of waking up early on a Monday morning would probably drive me to toss and turn most of the night. Nowadays, waking up early isn’t so bad anymore.

While still tired, I know that I get to wake up and see my son who is always happy to see me in the mornings. There is no better feeling than seeing him recognize me and smile uncontrollably. It makes my day. Waking up early also lets me get a head start on my day so I can aim to be home earlier to see him before bed time.

On top of all this, I’ve realized that starting my day off with feeding and playing with my son changes my mindset. Put simply, instead of checking my phone and emails first thing and being stressed all morning, I need to be present to take care of my kid first and foremost. It’s obvious but easier said than done… but starting my day with Colin puts me in a better mindset throughout the day.

I wouldn’t go off and call myself a morning person still, but I’m getting there.

February - a month of rest

I spent the last 36 hours or so recovering from my trip from New York. The first two days of the trip and nights were hyper focused on rest and work. I wanted to be sure to get the rest I needed so I could maximize my time with the team in the 2 short days I had with them.

After a good couple of days with the team, I decided to reward myself and meet an old friend on Thursday before my flight out on Friday. Of course, we did what old friends do in New York and caught up for a bit too long and over too many drinks. I had a blast but my Friday trip home was that much harder.

The recovery lasted well into last night. Unfortunately nowadays in my mid-30s with a kid, you either get to choose rest or social life.

My January was about social life as Sophia and I explored traveling with Colin. We wanted to make up for a stressful December so we took trips to Monterey and Lake Tahoe. And I took a work trip to New York for the first time. It was a lot of fun but I’m feeling the exhaustion now.

February will be the month of chilling and rest. I’m looking forward to being home and focusing in on spending time with Colin and getting work to get a spot.

Secfi New York

We started kicking off our office search for a more permanent space here in New York a couple weeks ago. We had about 14 options on the table and narrowed it down to 5 to view in-person which we did yesterday.

It was a fun afternoon with some members of the team. Sometimes at a startup, you’re so deep in the work and grinding that you forget that there’s a lot of other fun things that come along with the startup. One of those things is building out an office.

A good office space in a convenient location is critical to having people actually come into the office. We’ve been in a coworking space for the last few years and everyone has struggled with space and places for calls. Not exactly an inviting reason to come into the office.

We’re happy that’s changing here in the next couple of months when we have our own space. After going through this process in San Francisco, I’ve finally gotten pretty decent at finding offices.

First, we’re making sure we have enough room to make hires in the next year or two, but not big enough in our absolute bull hiring case. More space is not always better. If we somehow outgrow our space in the next 2-3 years, that’s fine and we can decide to move the team then. But having 10 people in a 30 person space makes everything feel very empty.

Rather, we’re looking at places that can sit 15 comfortably and then fit up to 20 with extra work. That should be more than enough space for the next year or two and also allow people to come visit from other cities.

We’re also prioritizing location. Paying $50 a square foot in Flat Iron vs $25 a square foot in FiDi is an okay expense for us. We want to create a culture where people want to come into the office, not because they need to. Location matters for people’s commutes as well as overall enjoyment of the space. I’d like the team to have the best lunch and happy hour options.

Lastly, also feng shui matters. Our last office in San Francisco had gorgeous views and was massive, but felt hollow. We had tried to decorate it and build it out the right way, but the pandemic delays and awful lease terms made it not worth it. This time around, we have two people from our team who love interior decorating and I’m happy to let them take the reins here. They understand the importance of building the office out the right way within a budget.