Tough decisions and conversations

Whether it’s deciding to let someone go or pulling the plug on a project, one of the biggest lessons I’ve learned from my 6+ years working at a startup is that tough decisions need to be made quickly and decisively.

The natural inclination for people is to delay or procrastinate that decision. It’s natural as it’s often easier to push things back and hope things fix itself out in the long run. It never does unfortunately.

For those reasons, it’s best to just make the decision and get it done. The conversations are never fun. There’s a human aspect to all this and often times these tough decisions impact individuals directly. But for the best of the company and that individual, it should be done quickly rather than a death by 100 paper cuts.

Time for a recharge

I’ve been running on fumes since December. I kept telling myself that I’ll take some time off when things slow down in January, but I’m sitting here mid-January and so far it’s been another busy 2 weeks of work.

Sometimes you need to hit rock bottom to realize things and unfortunately that’s what happened to me yesterday. I woke up exhausted and just generally negative about everything. I struggled through the day with some tough anxiety.

Simple tasks were just much more difficult and it was hard to focus for long periods of time. My run that serves as a stress killer and quick fix ended up being the most I’ve struggled in a run in months. Rock bottom indeed.

The toll of a newborn along with a stressful job doesn’t make things easy. Being a first time father adds fuel to the fire. Going forward, I know I need to do a better job managing my time and schedule. It’s just not sustainable to do what I used to pre-kid anymore.

For now, I’m going to take the rest of the week off after tomorrow morning. And possibly some time next week as well. There may not be a better time given things are slow and I need to take advantage versus creating more work for myself to stay busy.

It’s time for a recharge. I’ll be a better Dad, husband, and colleague once I do.

A sense of normalcy

Sophia and I had a fun weekend that we’re unfortunately paying for now. After over 2 months of new parenthood, we decided we needed a break.

Sophia had a girls dinner on Friday night and I had the guys over for drinks. It was a nice escape for Sophia and it sounded like a fun night. For myself, I had Colin still but it was also nice just having the guys over for drinks and watching football like we normally do.

On Saturday, Sophia and I hosted our “annual” crab feast for everyone. We had 8 friends over to our place for an afternoon and evening of crab and drinks. Colin was the star of the show and it was great to have all the friends over hanging out with him.

Having a kid there still makes things different but perhaps for the first time since Colin was born, it felt like things were “normal” as in the way things were before Colin was here. Of course, part of our journey now is understanding that there’s a new normal and getting used to that life style.

And yes, we’re paying for it today. Even with early bed times, the lack of sleep adds up. Spending the entire weekend socializing makes the next couple of days that much harder. For that reason alone, we may not be having many of these weekends anymore.

For one weekend though, it was a nice break.

Triaging the right partners

When you work at a startup, time is the most valuable resource. There’s just simply too many things to do at once and you need to prioritize accordingly. It’s always going with the highest value projects and deals.

We’re always trying to make sure we triaging the best deals. There’s always a trade off between amount of work and deal impact for us and finding that balance can be hard. Doing a sizable deal into a target company is always ideal, but if there’s complications that’s going to require a lot of work, we need to weigh that. Same goes for any projects we take on as a company.

One area that I need to really get better with is making sure we triage the right partners. Put simply, there’s some partners we work with that are great and worth the effort of building a relationship. They see the mutually beneficial aspect of working together and we help each other.

There’s others that are purely transactional and only come to you when you need help. Like in life, you don’t want to be friends with that person that only comes to you when you need something.

We’ve historically cast a big net here at Secfi in terms of our partners, but we’re at the point where it’s time to pick and choose better “friends”.

Losing your independence

So far one of the hardest things about being a parent is coming to terms that I simply can’t do much else besides parent anymore. There’s no going out to dinner anymore or grabbing a drink with friends after work. Well at least not often.

In my 34 years on this planet, I’ve lived mostly independent doing what I want. Things changed a bit once I moved in with Sophia, but still if I wanted to grab a drink with friends, it would just need to be a simple text message.

That all goes out the window once you have a kid. As much as I’d love to try this new restaurant, Colin needs to be in bed by 7:30pm to ensure he has a good night sleep. We could try to do an early dinner at 5pm and bring the kid, but it’s not the most pleasurable experience brining a 2 month year-old to a restaurant in the fussiest part of the day.

Sophia and I are trying to decide if we want to take a quick weekend road trip to Monterey in a couple weeks as well. Normally, this would be a dream weekend for me to get away and do something different. But of course, we’re thinking twice about doing it given that we now have a kid.

It’s a tough transition for sure and I’m still getting used to it. Seeing my son smile at me though makes it all the better. At least I have that to look forward to.

U.S. Digitalization in 2025

I spent over an hour at the Post Office today applying for a passport for my son. I suppose in the grand scheme of things it wasn’t the worst experience or the biggest time suck, but I showed up on time for my appointment only to wait 45 minutes before being helped.

As anyone would guess, the application process was filled out on paper and we had to print everything to bring to the post office. Once there, the post office worker had to hand print more things to finish the application. When I left, I could tell her was preparing the application to be mailed to the Government.

This is the year 2025 in San Francisco nonetheless and we still have yet to find a way to digitalize passport applications. Of course, this isn’t the only example of where our Federal, State, and Local governments are severely behind in tech.

I have no interest in helping fix the government’s issues, but I imagine that with proper incentives in place, there would be many entrepreneurs who would step up to fix these antiquated systems and processes.

The year of the degenerate

Life moves fast. I can’t believe it’s already 2025 now. I remember sitting in a management team offsite about 3 years ago outside of Amsterdam with the team. It was Q1 2022 and we were planning for the potentially bumpy road ahead.

Like everyone else, we didn’t realize just how bumpy it would be. The first interest rate hike was on March 2022 and like that, the startup and VC market started to grind to a halt. The last 3 years in VC and startup land have been tough. Valuations dropped significantly and the IPO market has been largely closed.

It feels like everyone is chomping at the bit. We have Bitcoin trading at near all time highs and lots of people seem to be having fun gambling with Memecoins. The degenerates are out in full force in crypto world. That has yet to translate to the startup/VC world and retail stock trading.

I expect that to change in 2025. With the IPO window seemingly heading for an opening shortly, more money will start flowing to the pre-IPO world. People are sitting on their hands ready to deploy capital.

The retail stock trading world seems also ready to participate. While the public markets have largely been held up by the largest companies, I expect more money to flow to growth and smaller cap companies this year.

It’s going to be a year of the degenerate. Everyone can be a trader and people are looking for a good excuse to gamble.

January

I used to think January was the most depressing month of the year. The fun of the holidays is over and winter is in full force. School and work is back in session, and it’s dark and cold. Nowadays, I love January as it’s a reset month for me.

With the holidays behind us, I use January to get back on a good healthy schedule. I eat better, I exercise more, I drink less, and I try to sleep more. My body gets a nice reset.

January is also a time to get back to a routine. With the holiday craze with travel, family, friends, etc. you lose track of time and it’s all a blur. In the new year, I get back to a much more predictable routine.

It’s also a good time to take a step back from work and look at everything we accomplished in 2024. We’ll celebrate our wins and figure out how to learn from the losses. In the heat of things, it’s difficult to really take a step back and look at things from a high level.

Lastly, it’s a great time to plan for the year ahead both personally and work wise. I start to get more excited about life during this month as I start to look ahead to everything that’s in store for us.

Bring it on 2025

I wish I could sit here saying that I’m feeling refreshed, but truthfully I am exhausted from life and work right now heading into the first weekend of 2025.

It’s been fun having the in-laws here, but there’s been very little downtime with them and Colin. I had a pretty good holiday season, but with a lot of activities also comes a lot of stress.

On top of that, we’re working through the constant ups and downs of a 2 month year old newborn. We have some amazing days and nights, and then some just brutal ones. Last night was one of those brutal ones and needless to say, I could use a nap this afternoon.

Lastly, work during the holidays are much more stressful than I had wanted. I didn’t get those magical couple of weeks of rest that I was hoping for.

Regardless, life goes on. For better or worse, this is likely to be the new normal for me. But nothing worth it in life is easy.

I’m going to have to be better across all fronts in 2025 — more unselfish, more disciplined, etc. It’s a new challenge, but one that I am excited to take on.

For now, I’m hoping to take January as a nice transition month for myself and Sophia. Things should slow down a bit for work and Colin will be starting to hit that age where things are slightly more predictable. It’ll be a good month to get my life back in line.

2025 Goals

If last year was the year of getting myself right and being selfish, this is the year of focusing on my family. Knowing that I’m going to be absolutely swamped with the move to New York while trying to learn how to raise a child, I want to keep things simple. It’s a transition year for me and my family, and the big thing is to be present and not take on too much.

Be Present

I hate to admit it but I’m addicted to my phone. It’s not just social media but also emails and Slack. I’ve caught myself emailing while feeding and playing with Colin. And I feel like shit. My first goal for 2025 is to be present and put away my phone when I’m with Colin. These are special moments that won’t last forever and I want to make sure I’m here for it.

Be more Patient and Chill Out

If the first two months of Colin’s life is any indication, my known impatience is heading to unprecedented levels. The lack of sleep and personal time has really made me a much less pleasant person to be around. I can sense it and I’m sure Sophia and others can sense it as well. I need to become a better partner and friend in 2025.

That means chilling the fuck out a bit more and becoming more understanding. Parenthood is hard and I need to be better when it comes to being a partner.

Teach more

One thing I’ve learned about myself in the workplace is that I’ve become much more of a boss rather than teacher. The last couple of years has required me to step up more and grind out more work. And my focus on developing my team has slowed down a bit. I want to flip that in 2025 especially as I start becoming a regular figure in the New York office.

For the better of everyone and Secfi, I want to make sure to become more of a teacher in 2025.

2024 Goals in Review

I don’t really believe in New Year’s resolutions. They are things people say and usually break after January. Rather, I believe in goals which are things that are achievable over the course of a year if you set them and put your mind to it.

Last year I set 4 goals and I’m fairly proud of how they turned out. Diving into each specific.

Become conversational in Mandarin

This one was probably my biggest miss in the year. After taking a class in 2023, I vowed to try harder in 2024. I continued my Duolingo lessons but I wasn’t committed. I adjusted course a bit in December and decided to start the lessons over again with a focus on becoming more conversational rather than trying to score in Duolingo which has helped.

However, as I sit right now. I know quite a few words and can understand tidbits. But I still struggle to actually converse with anyone in Mandarin. I give myself a D here.

Get sleep and feel good again

I wanted to start feeling healthy and good again in 2024. My transition from early 30s to mid 30s was rocky to say the least.

I got my sleep at least under control in 2024 and slept more. I drank less and attended less events than I have done in the past. Overall, I’d give myself a B here.

Be selfish

This was the year that I was going to be selfish with Sophia and try do as many things as possible for ourselves before we had a child. Sophia and I did travel quite a bit and we were able to focus on ourselves. Of course there’s always more fun things to do in the world, but given everything, I’m happy with the way this turned out and give myself a B.

Start exploring cash flowing businesses

For my professional development, I wanted to start learning more about cash flowing businesses as a potential next step. Perhaps I would run a side business in the future or buy a business when my time at Secfi comes to an end.

I’ve spent a good amount of hours reading about the various kinds of business and the challenges small business owners face. I’m proud of the work I’ve done here. I’ve gotten myself a good mental model of what I’d potentially be looking for if this were to happen.

I still want to learn more, but I’m happy with the work I’ve put in and give myself an A.

Life is good and unfair

I’ve been catching up with a lot of old friends over the last week. My best friend asked me today if I thought my 2024 was my best year.

It was a hard question to answer, but I think with the birth of my son, I’d say it defaults to being a yes. There is nothing in the world I care more about than my son and I will do anything for him. All that said, it’s been far from a perfect year as we’ve dealt with a lot of bad along with the good.

My father in-laws health and recovery from the stroke has been less than ideal. We had hoped he would be further along in his recovery, but brain injuries are difficult and unpredictable. We’re overjoyed to have him here with us still after such a big injury, but also realize how fragile life especially with our aging parents.

On another front, one of my good friends also told us yesterday that her younger brother has brain tumors. It was absolutely devastating to hear as he was a survivor of pediatric cancer. It is heartbreaking on so many levels and hearing stories of a 30 year old who has dealt with so much in life already talking about his potential early death really took a toll on me.

In a year of so much joy for me with bringing Colin into this world, I also realize just how fragile life is. Life is just unfair at a times. Horrible things happen to good people who deserve it the least.

I am grateful for everything I have in life and this holiday season, I’m counting my blessings. It’s important to remember that nothing in life is guaranteed and we need to live.

Colin's first Christmas

It was an exciting last few days with Colin’s first Christmas. We spent Christmas Eve at my Dad’s house with the in-laws in town as well. The whole gang was together. Most of my closest family members were there and as expected, Colin was the star of the show.

He did great spending the day at Grandpa’s house and enjoyed being held by pretty much everyone. Watching my Dad get excited to hold Colin was a moment I’ll always remember. It was a special time for sure and one that we’ll remember.

It was also an exhausting few days. Our worst comes out when we’re tired and I can’t say I was the best version of myself at times. The sleep debt adds up over time. Once you add in social events and alcohol to the mix, and it becomes a cocktail of exhaustion.

I finally feel a bit more normal today after getting some decent rest last night. I was able to get some work done this morning and I’m going to try to get a quick workout in after lunch. Work seems to be finally slowing down and we can see the light at the end of the tunnel.

My hope is that by Monday we’ll be completely wrapped up for the year. Then I can focus on recovering and taking a break. I’m clearly tired and burnt out and I need some time so I can be the best version of myself again.

The Holidays

The Holidays are always a mixed bag for me. The work, travel, and family stress can definitely add up in this period. It’s also been a time of personal loss for me as my mom and grandmother both passed away right before the holidays during my childhood.

Despite all that, I’ve always loved Christmas. Some of my fondest memories as a child were around the holidays. I loved decorating the Christmas tree every year. I loved going downtown with my Mom to all the fun holiday shops. And I especially loved getting a lot of presents every Christmas.

This year, we have my in-laws in town which has been fun in many ways and stressful in other ways. My father in-law’s recovery from his stroke last year has been up and down. It’s sad to see them in this state, but at some point, we have to just be happy that he’s still here after such a big stroke.

We’ve had a lot of fun. Having our families hang out has been a special time for all of us especially with the newborn. I also really enjoy taking them out to places that I love in San Francisco. But yes, nothing is easy nowadays with aging parents and a newborn.

This year especially I’ve been really relying on optimism and my meditation to get me through. I’ve had to be more patient than ever before which is one of my weaknesses. It’s a special few weeks for our families and I want to make sure to focus on all the positives as we don’t know how many more of these times we’ll have again.

Time, stress, and work

It’s been a tough couple of days for us. After a new good days, Colin seems to be going through his 6 week growth spurt and has been demanding an impressive amount of milk throughout the day and night.

We also have Sophia’s parents here in San Francisco for the holidays. It’s been awesome to have them here, especially since what they’ve been through the last year, but it adds another element to our already busy lives.

My hope of being pretty much unplugged for the next two weeks seems slim at best right now. Regardless, I’m hoping to keep the work to a minimal and be able to spend a lot of time with Colin, my parents and my in-laws.

I’m not sure when we’ll be able to get everyone together here for the holidays again. The work will always be there, but times like these won’t. It’s important for me to remember that as we enter the heart of the holidays.

Catering to the non-customers

One product improvement that we’re looking to tackle in early 2025 is improving the product experience for the customers that we reject.

Of course, our focus should be around bringing in customers at our target companies, i.e. the ones that can generate revenue for us. That has been and will always be our focus. However, there’s something to be said about creating a great experience even if we can’t work with you.

We have a difficult business and product. Our tools are available to all startup users for free so anyone can create an account at Secfi.com. From there, we offer two products Wealth and Liquidity solutions.

On the Wealth side, technically anyone can be a client, but the minimum cost pared means that only individuals with a lot of equity would benefit the most. Our services are personalized and 1:1 so there’s an inherent cost of assigning a personal advisor.

On the Liquidity side, we can unfortunately only work with late stage companies at this point. The subset of companies approved for a secondary or financing is less than 1% out of all the companies out there. This creates a difficult situation as quite often, people sign-up with the expectation that they should get funding.

We always respond to every request so we do not ghost individuals. However, there’s only so much feedback we can provide to every company/individual we reject. We simply just do not have the bandwidth. Most companies are just simply too early.

We can do a lot better though. There’s a lot of improvements that we can make to ensure that customers get as much info as possible. While we cannot hop on calls with every requests that we reject, we can improve our expectation setting and communication. This is one of our projects in Q1 next year.

This blog / journal going into 2025

Over time this blog has become more personal than work related for me. When I first started trying to write something daily, it was primarily driven by my desire to get better at writing for work and get comfortable with writing online.

As the years have gone on, I’ve found a lot more joy writing about my personal stuff more often than work. This blog has become more like a journal for me. It’s therapeutic and has became a place where I can write down my thoughts.

I suspect the other reason is that I’m just buried in work most days and the last thing I want to do is write more about work while living in work. I also help write our newsletter that goes out biweekly so most of my work thoughts have gone to there.

Going into 6+ years of writing this nearly daily, I still enjoy it and I want to continue doing so. I do hope to write more about more business/work/market topics though next year. I need to do a better job at consolidating those thoughts more like I do my personal thoughts.

Much needed break from social media

I probably hit my low point since Colin was born on Saturday. I was just exhausted from last week and it all hit me hard once I got to the weekend. The last two nights were great though and I’ve got a pep in my step this Monday morning.

It might be wishful thinking, but I’m hoping that now at about 6 weeks old, Colin has gotten over the early newborn sleep issue hump. He slept in one 4.5 hour stretch last night and has been going to bed and staying to sleep much easier the last few days. There will undoubtedly be setbacks, but I’m hopeful we may have gotten him to get flow.

On another note - one great byproduct of having a kid is just simply not having time to doom scroll social media. I haven’t deleted X or Instagram, but during my free times I’ve gravitated to reading more articles and playing some of the NY Times puzzle games daily.

I’ve had to become more productive since Colin was born. The lowest hanging fruit to buying more time in the day was not doom scrolling social media. I’m glad that’s happened naturally for me.

It’s been awesome and the impact on my happiness and mental health was been noticeable. Put simply, I just feel more optimistic about the world and less angry in general without spending hours in X or Instagram.

It’s a refreshing break and I recommend everyone do the same.

Don't be a d*ck

My number one rule in working with clients and partners is to not be a dick. Admittedly, it’s tough at times and there have been many moments where I want to give someone the cold shoulder or tell them to screw off. I haven’t been perfect, but I’m proud of myself for biting my tongue.

For me, it’s the simple things in my short time on this planet that may make a difference. Trying to help people when I can. Giving people the honest truth. Apologizing when I screw up or make a mistake. Being the bigger person.

Of course, we run into people all the time that don’t have that same mentality. Whether it’s someone who tries to walk all over you or use your time without the right intentions, it happens all the time. It’s often really frustrating and as much as I try to not let it get to me, it does at times.

I never really understood it. People usually want to work with people they like so you would think they would have learned by now. But perhaps they’re just miserable people all around.

I try to remind myself that for every shitty person, there are 10 other great people that I’ve enjoyed meeting and working with. This job is worth it for the 10 awesome people, not that one dick.

The new normal

After spending the first 3 days of the week from the office, I worked from home today to help Sophia out with Colin. While it is nice being around Colin and it’s been good giving Sophia a bit of a breather, it hasn’t been easy. I’m writing this at 4:25pm right now and I’m at step #1 of my checklist.

Of course, part of that is just simply craziness and calls at work that took me away from my to-do list. But Colin does what he does, and that’s making things more difficult.

My 7am and 7:30am calls were done with a noisy baby in the background feeding as he decided he wanted to sneak an extra meal in.

I wasn’t able to eat any breakfast until later in the morning as he didn’t want to get back to sleep.

The laundry, dishes, and prepping for his meals also took more hours out of my day and away from work.

I was hoping to be through my work and ready for the Niners on Thursday Night Football in 30 minutes. But alas, I’m probably playing catch-up for the next few hours during Colin’s naps.

This is the new normal with a kid. I had prepped on being more stressed and tired. That is going okay. But the drop in productivity aspect is stressful. That’s the sacrifice that parents have to make unfortunately and one that I need to get used to.

Things will get a bit easier with time and childcare help, but there will be more things that come up. For now, when I’m working from home, I’m going to have to squeeze in work where I can. That’s during naps in the early morning and late evening. I’ll also need to maximize the days I get to go to the office much more.