Much needed work breaks

I needed to get my mind a bit right again yesterday so I took a break in the afternoon to go to the gym and unleash some steam. It was a really nice moment for me to unwind for an hour after a stressful morning. It’s really easy to spiral when your mind is not in the right headspace and that’s not productive for my health nor my work product.

Taking a break to work out always gets me in a much better mindset. Sometimes I just need to step away from the screen for a bit and burn off some steam whether that’s through meditation, a walk, or working out. I had been doing this since even the early days of my career working 70+ hour weeks.

My coworkers thought I was crazy going to take a break at 5pm to come back to the office at 6:30. Afterall, that’s an extra hour and half of work that could be done and some extra sleep. But I always found that I was almost always more productive after I got back. That project that would have taken me an hour could take me 20 minutes. Or that problem I was stuck on was suddenly not a problem anymore.

Yesterday, when I got back to the office, it was business as usual and I felt reinvigorated and ready to grind again. Things are trending on the up and up heading into the weekend. I just need to have all my brain cells in-tact to take advantage of the opportunities.

Mental strength

These next few weeks and months are going to require a lot of mental strength to get through. The trade war news and market volatility is admittedly taking a toll on me right now. This isn’t a fun time for anyone in finance right now. CEOs and companies are taking a lot of action and changing 2025 plans. IPOs are likely to be on pause for now.

I don’t have any control of the markets, but the markets always have an impact on us given the nature of our business. It’s a stressful time and everyone I talk to in the industry feels the same way.

I know what I need to do in the next few weeks/months. And that’s to dig in, keep my head down, and work hard. Positivity is going to go a long way for me and staying out of the negative news cycles is step one. Of course that’s a lot easier said than done as I want to scream into a pillow right now.

At this point, I’m trying to remind myself that everything will be fine and this is a long journey of a lot of ups and downs. Hopefully I’ll be able to look back at this period and be glad that I went through it. And also hopefully there’ll be a lot more ups than downs in the future.

Saving for a rainy

The rain is back today in San Francisco. We’ve had what feels like a rainier winter than normal and it looks to continue the rest of the week. I suppose the rain is a good excuse to stay in, spend time with Colin, and rest.

Metaphorically it continues to be a rainy winter in the markets. Trump’s trade war has everyone spooked right now and smart people I talk to are saying that we’re either already in a recession or we need to let it play out because it’s all part of the plan. I have no idea how long this will last or the outcome.

I wouldn’t say I’m a fiscally conservative person in the grand scheme of things. But now with a young child to support, my mentality is now to save for that rainy day. I’m going to continue to live my life, but I’m taking more action nowadays when it comes to things like budgeting.

For example, my budget for housing in New York is going to be much more strict. We’re likely going to be adjusting our budget downwards and trying to aim for the lower end of that budget rather.

We’re in a fortunate position that we do not need to panic about finances right now as we’ve done a good job saving. But I don’t ever want to not be in this position in the future. It’s best to be conservative and safe here, than be worried down the road if things do really turn south.

Colin's first day with a nanny

Today was Colin’s first day with the nanny as Sophia heads back to work. We feel like we made a great hire in our nanny and Colin seems to really like her. However, there was quite a bit of anxiety for us between yesterday and today.

Deep down, we know Colin will be fine and this is a normal thing parents go through. Colin will need to have a nanny and eventually grow into daycare and then school. It’s part of life and growing up. But it is hard officially losing control of his day to day. We’re just reminding ourselves that this is for the better and will be part of growing up.

I am excited for Sophia to go back to work again. She needs some time away from Colin for her own sake and I think she’ll start to enjoy parts of work again shortly.

Healthier habits

I had a rough weekend unfortunately. The sleep deprivation and stress with work and life really just caught up with me. I was exhausted coming back from Hawaii last Monday and went straight into a mountain of work. There was a lot of late nights and early mornings and I never felt good most of last week.

I did my best to try to catch-up on sleep and life over the weekend but my other full time job of being a Dad can’t really be put on pause. We didn’t do much over the weekend and it was unfortunately mostly spent just tiredly hanging out with Colin. There was a lot of low motivation and slugging around.

I’m finally feeling decent again this Monday morning, but it’s going to be a journey these next few weeks to close out and quarter and I need to make sure to take care of myself. That starts with getting back to healthier habits like reading before bed and moving my bed time earlier.

Over the last few weeks, I could tell that Sophia and I started doing more and more with life as we got more comfortable with Colin and he started getting on a good schedule. That meant more going out with friends, staying up later than the early days, watching more TV, etc.

All that stuff is fine of course, but it adds to our exhaustion levels. It’s time that we peel some of that back a bit. Like with most of things, it’s the simple things in life.

Keeping my head down

I’m glad it’s Friday. I had a pretty good birthday yesterday. Unfortunately I was just slammed at work and running on fumes most of the day. Sophia and I were able to go out to a nice dinner at Ernest while one of my friends watched Colin. I was really grateful for the opportunity to go out to dinner again, but I was half asleep pretty much the entire night.

The transition to crazy work schedule with a newborn hasn’t been easy. The work stays the same and I have less hours to get it done. My days are longer now to accommodate the schedule, but there’s still less hours than I had to focus on work. It’ll continue to be a challenge and I really need to make sure to use my weekends to rest and spend time with Colin as much as possible nowadays.

On another note, everything just feels crazy right now. Trump and his administration are following through on their tariff strategy which is causing a lot of uncertainty in the markets. There’ll be a lot of short term pain unfortunately. One of which is a possible delay in the IPO window. That is frustrating to say the least for all of us in the startup world.

The uncertainty is causing a lot of confusion and volatility. No one really knows how this will all end. I’m vowing to try to stay away from reading every news headline out there right now. It’s not good for my mental health. I need to keep my head down and stay focused on the goals and what we can control.

35

I am 35 years old today. At this point, I don’t know whether to feel young or old. In my mid 30s, I still feel young at heart. At the same time, my body is often telling me otherwise. This birthday is perhaps a little extra special as I am a Dad now and birthdays will become a much bigger thing in our household going forward.

Today, I am feeling incredibly blessed and grateful. My life has been far from perfect, but I’ve lived a great life. I hit the birth jackpot and was born in San Francisco. My parents gave me many more opportunities in life than they had. I have a great and loving wife and amazing friends who I love and trust. Work is work, but I get to build a company with amazing coworkers who I respect, trust, and love working with.

I’ve been fortunate to travel to many places in the world. I’ve had great experiences. I’ve been fortunate that I’ve been able to enjoy my joys in life like food and golf. I hope I get many more years on this planet. And maybe most important of all, I have an amazing son that is healthy that I get to raise. Truth be told, I’ve lived a great 35 years on this planet and I do not take that for granted.

There’s a lot of shit to complain about in my life and the broader world right now. But again, I need to choose to remember that I live a great life and I need to be grateful for what I have.

In this 35th trip around the sun, I want to make sure to lean on gratitude and learn to complain less. Life is simply too good to be a curmudgeon and I hope to never turn into one, no matter how old I am.

Craziness in the world

Yesterday was a tough day for me. I was just exhausted from my trip and trying to get readjusted back to the mountain of work waiting for me. First days back after a trip is always more difficult.

On top of all that, it was a tough news days. The markets are reacting to the trade war and other global events. I have no idea how it will all pan out, but a lot of people much smarter than I am are a lot more pessimistic about it and the optics don’t look great right.

Like I’ve said since Trump was elected, I sure hope all this works out and his plan proves me wrong. All Americans could stand to benefit, but at this point, it’s hard to ignore the potential downsides here. That downside directly impacts all of us.

On top of that, there was news that someone I know and liked from our limited interactions was just arrested for fraud. This individual was someone I was excited to meet many years ago given his success in the business world. He was someone I admired from afar given what I thought was his care for the world. He seemed like a genuinely great guy.

It was disheartening to hear that he was arrested for fraud. Whenever these situations happen, they tend to make me more jaded especially in our world where people build businesses to better the world.

As always, I need to remember that there are good people out there and focus on the good and not the bad in this world.

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.