Feature Request

We currently use DocuSign for our eSignature uses and I often send 1-2 things per day to clients to sign. The process historically is to log-in to DocuSign, find the template, put in the info and send it to the client. Then send an email to the client letting them know it’s in their inbox.

Why are these eSignature services not built into any email clients for automation? It seems like an easy win that saves people a lot of time and annoyances. I’d love to open Superhuman, and then have a DocuSign integration that allows me to send a doc directly from my email client. AI could be used to populate the fields as well.

I’m not sure why this hasn’t been built by DocuSign or any other eSignature company at this point, but it feels like a no-brainer to me and I would switch providers to the ones that have this built in.

Stability please

After 3 nights of good sleep, I’m finally starting to feel normal again. My motivation and happiness is back, and I no longer feel like a brain dead zombie. That was a rough couple of weeks for me and needless to say I’m glad that’s over.

In other things I’m glad is over, it appears that the market has rebounded to a positive year after Trump’s self-inflicted trade war began. Our President seems to have folded on his bold plans and the market has adjusted.

Of course, we’re not in the clear yet and who knows what Trump will do next. But it seems like Trump has shifted his focus from destroying the economy to meeting other countries in the Middle East and getting deals done. At least this gives us a bit of a breather on the market side for a bit and we can get back to growing the economy.

For now, some stability is exactly what I need in my work and personal life and for the first time in awhile, I feel like I’m getting a bit of it. Life is good.

SF vs NY

It’s pretty funny just how many Californians and specifically people from the Bay Area are here in New York. I walk around my neighborhood in Brooklyn and I never have to go far to see a SF Giants hat or a Warriors T-shirt. Apparently a bunch of folks who have moved into my building are from San Francisco.

I have no actual data on this but I’d guess that there’s many more folks moving from SF to NY at this point than the other way around. At this point, NY is fully back. Things are looking even better than it was when I left in 2018. New buildings and restaurants are opening everywhere still. It feels like it’s even more lively than it was when I left.

San Francisco is just on it’s way of making it’s way back. I really love what the new Mayor is doing there working with businesses to come back and rebuild the city. But at this point, it’s a far cry from where New York is and likely going to be at least a few years until we start to see SF get back close to where it was pre-pandemic.

The energy in SF just has been dead the last few years with no one going into the office anymore. The FiDi and downtown area feels at best 25% of where it once was. It doesn’t feel like a ton of construction is happening and restaurants seem to be closing more than they are opening.

Of course, San Francisco will never be New York for better or worse. The beauty about San Francisco is that it is much more chill and relaxed than New York. But at this point, if I was in my 20s working my first job out of school, I would much rather be in New York than San Francisco.

I am excited for how the city changes in the next few years while we’re in New York though.

A new chapter

While we got to New York on Monday, it’s actually starting to feel real today. We dropped Colin off at his daycare for his first day. He went in smiling and was ready to be a big boy. The daycare uses Brightwheel to send us updates on Colin, and I’m loving the experience so far. As much as I love spending time with him, it is nice for Sophia and I to have some time and help with childcare.

I also commuted into the city for my first day in the office. When I lived in New York during the pandemic for a couple of months, I signed us up for Rise in the Flat Iron. Now that the space is closing this summer, we’ll be moving to the FiDi at some point this week or next. It’s yet another move to handle, but this time around I’ll have a lot more hands and we’ll definitely be hiring help to do everything for us.

It does feel like a new chapter began today. Things will definitely get a lot more difficult at times managing commutes and strict daycare drop-off/pickup times. But things will definitely be a lot more fun and exciting living in New York again.

We made it

We all made it to New York and the movers are coming with our stuff in about an hour. The nightmare of a cross country move with a 6 month year old is nearly over and I couldn’t be more excited to get back to a normal schedule.

Monday/Tuesday were brutal days as expected. Sophia and I worked hard to pack up our apartment on Monday, and then took a redeye to New York. Colin was a champion and had very little fussiness. Naturally, he slept the most out of all of us. We landed at about 2:30am PST and got Colin on schedule while Sophia and I slugged through the rest of the day.

I’m stoked about being here, but it didn’t take long to get a reintroduction to New York as we had to make a Costco run yesterday. That was probably the last time I’ll ever go to Costco in Brooklyn.

I’m hoping after today, we’ll feel a lot more settled and be able to actually enjoy being here. I cannot wait to sit on my couch and watch TV tonight. My back could use some support after a week and a half of sitting on the floor.

Countdown to New York

Another day and another moving annoyances. My car pick-up has been pushed back again and my schedule is now in-flux. The stress and exhaustion of the last few weeks is weighing on me.

I cannot wait until this time next week when we have everything and we’ll hopefully get back to a normal schedule. On my next cross country move, I’ll likely look to pay more of a premium for folks to take a lot of this stress of my hands.

Luckily work hasn’t been too crazy and I’ve been able to move the ball forward despite having a crazy schedule this week. I’m thankful for having a great team at work that’s been able to cover for a lot of my stuff this week.

I’ll need to make sure to use this weekend to get some R&R before a big travel day on Monday. On the other side of that travel day is hopefully a lot of fun and some time off to enjoy the city with Sophia and Colin.

Fire fast

One thing I’ve learned in my startup career is to always fire fast and hire slow. It’s the cliche statement that any experienced operator will tell you, but unfortunately most people need to live through a tough situation before they actually take action on it.

It’s simply just hard to fire people as there’s a human aspect to all this. We learned the hard way early on at Secfi with probably a couple individuals that needed to be let go months after the hire when we realized it wasn’t working out. As per the script, we let it go many months too long and it caused a lot more issues than it needed to.

Of course, the lessons from work could also be applied in real life. We hired a temporary nanny for two months in San Francisco as Sophia went back to work. We knew it was temporary as we were moving to New York and was upfront about it. We hired fast as it was just temporary and the first person we met seemed to be okay and had a good referral from the last family.

After the first week, it was evident she was not great. She complained a lot, made a lot of excuses, and did not seem to be on a good rhythm with Colin. We probably should have made the switch early on, but since it was temporary, we decided to tough it out.

She took good enough care of Colin that it wasn’t an urgent need to let her go. But she couldn’t stick to our schedule and make excuses for why she couldn’t. We now regret that decision and should have made the change early on.

Of course, with her last day tomorrow, she called in sick this morning. It seemed like the perfect day to call in sick as it was a payday and she had only 2 days with us remaining. While I wanted to believe it was innocent, we also noticed that she took her stuff with her yesterday when she left so this was clearly planned.

At minimum, we now know for future needs. But sometimes we have to learn the hard way.

Things don't always go to plan, and that's okay

Well the movers came and did a pretty good job getting everything out and on the way to New York. The service was right for the pricing but I wasn’t pleased with the carelessness of the way they handled things including causing a good amount of smudges on our hardwood floor. But you get what you pay for.

I wish I was sitting here feeling amazing about everything, but sometimes your plans just don’t pan out exactly the way you want it to. I had scheduled movers for yesterday with the hopes that everything would arrive on Tuesday or Wednesday next week leaving us with our stuff and a week off. Unfortunately they let us know that the stuff wouldn’t start the journey to New York until Friday and the earliest we’d get it is Saturday.

On top of that, the car pickup I scheduled for today got pushed back to Friday so again we’ll likely not have a car until the back half of next week. On top of that, our mattress has yet to ship so we may not have it ready for Tuesday.

So all my plans to basically have my stuff as soon as possible in New York while we’re out of office and getting settled has completely gone out the window. And the icing on the cake is that we may not have a mattress to sleep on when we arrive.

As a type-A planner, the stressful week has gotten even more stressful and my anxiety is through the roof right now. But thus is life and we’ll need to adjust as needed. I suppose in life part of having a good plan is making sure that your contingency plans are also good.

Luckily, Sophia and I are in a good position with friends in New York. In a worst case, we can always go to a nearby hotel that shouldn’t be too bad. As for our stuff, I had hoped we could casually unpack throughout the week, but we’ll just need to take some time over the weekend to do the big things and then just live with some boxes for the near-term. It’ll all work out, but it’s annoying nonetheless when things don’t go to plan.

Time to downsize

The movers are here and doing a great job getting all our shit out to New York. I’m happy to get everything out and start the process finally after weeks of packing. Unfortunately we’re about 50% more than our estimate of stuff.

As someone who likes to live as minimalist as possible with material goods, I have no idea how we accumulated so much stuff over the years. A big part of that is the kid, but I can’t deny that we have a ton of clothing and other goods that is probably excessive.

It’s probably time to try to downsize and get rid of as many things as possible while we’re in New York. The good news is that we’ll likely be forced to as our living situation is much smaller than it is in San Francisco.

It’s a done deal now, but we’ll probably have yet another garbage and donation run while we’re out in New York.

The return of San Francisco

I had an amazing and full weekend with friends and family. On Friday we hung out with my sister and family for a few hours before seeing friends for dinner. On Saturday we had our going away party and was able to see over 20 of our closest friends here in SF. And on Sunday we had a nice picnic on Angel Island to celebrate my good friend’s wedding.

It’s these moments that I’ll definitely miss while we’re back on the East Coast for a few years. There’s definitely a lot of FOMO right now especially as San Francisco is making a huge comeback.

I received a note this morning from one of the local city groups that I follow and there’s a ton of positive developments. Crime fell to it’s lowest point in 23 years and car break-ins dropped by 54%. Our newly elected Mayor has been doing a ton of great work in the city convincing cities to reinvest in San Francisco.

The road back from the lows of the pandemic have been especially hard for San Francisco, but I haven’t been this optimistic for the city in a long-time. I predict that when I finally do get back home, San Francisco is going to feel much like the bustling times of the 2010s rather than what we’ve seen from the first half of the 2020s.

Grateful

We’re just about 80% done with packing on our end. My allergies are gone and I actually feel rested and energized. I got a ton of work done over this week to set myself up to be largely OOO for the next two weeks. And it’s Friday going into a fun weekend of activities. Life is good and I am in a very grateful mood.

I am sad to be leaving San Francisco. We’ve been doing a lot during the move like getting rid of my plants that I got during the pandemic and finally throwing away some leftover stuff from our wedding. When one chapter ends, there’s always going to be some sadness.

Today, I’ve been really grateful for the last 7 years back home in San Francisco. Sophia and I came here and lived together for the first time. Got married here in SF and had our first child here. It feels just like yesterday when we went to our first Bay to Breakers a week after Sophia officially moved here.

I’m incredibly grateful for all our friends here and the experiences we were able to share with them. Being able to come home and watch my little sister grow into a teenager has also been special and I’m so happy to have been part of her life. It’s been a blessing being back home for the last 7 years.

Choosing a daycare

We’ll be starting Colin in daycare after we move to New York in a couple of weeks and we’ll need to make yet another decision as parents that could have a impact on Colin and our lives.

I am forever grateful that we are first time parents in this day and age of tech. We were able to do Facetime and Zoom virtual tours despite being across the country. We can sign-up Colin for a spot in daycare in just a couple weeks pretty much all virtually making our lives a lot easier.

Even 10 years ago, I’d guess we’d probably have to go and spend a day or two touring the facilities with no guarantee that he could start the following week. Thanks to tech, we’ll have things figured out by the time we make the journey east and be ready for our first days in the office the following week.

On our choice though - I feel like this is going to be a tough one as we balance location with facilities and care. Luckily, I feel comfortable with all 3 in terms of level of care and they all seem to have good reviews.

Unfortunately, perhaps the ones with the best facilities are far away and we’ll need to weigh adding 30-60 minutes to both our morning and evening commutes if we wanted to go with the ones further away.

Clarity

There’s just so much shit going on with our government right now it’s hard to keep track of. What seems like fake news is actually true, but there’s still a ton of fake news out there. The jokes and memes have been fire lately though.

The market is reacting accordingly and seems to make large movements up and down nearly every day. It does seem like business leaders have had enough though. Trump has folded in many of his initiatives so who knows what’s going to happen in the coming months ahead.

This uncertainty has been brutal for most of us investors in the private market side. A company that we know well has been planning on going public for the last few weeks and everything has been put on hold until there’s some clarity on what will happen. Unfortunately, no one can answer when that clarity will come.

Let’s all just hope that clarity comes before the long-term damage is done.

Mattress tech?

I just sunk a few thousand dollars into a brand new king sized mattress and nice sheets. It’s always painful incurring that big of a cost, but hey at least it’s something we use every day. As a consumer, I usually do an excruciating amount of research into making these large purchases.

Of course the cost is high so it’s important that you spend your money wisely, but almost as important is dealing with the hassle of not liking what you buy and having to deal with it down the road. I read countless blogs with a lot of skepticism knowing that they are often paid, and then supplemented that with hours of reading on Reddit. I suspect a lot of people in our generation do a lot of similar research.

I ended up choosing a Helix mattress for the quality and great reviews. Their parent company owns the factory in Arizona so we know that the quality is there. On top of that, the price of what you get is a fantastic deal despite this being a more expensive mattress comparatively.

The biggest decision that Sophia and I had to make over the last couple of weeks was to get the highest end version or the middle tier. The idea with the highest Elite tier is that you can replace the mattress pads and this mattress last for life. We ended up going with the middle tier Luxe version without that option.

Sophia had a great insight that mattress technology is rapidly changing with a lot of companies innovating. In 7-10 years, there’s going to be that new hot mattress that we’ll want to upgrade to and it’s probably not worth spending the extra $1,000 for that interchangeable mattress today.

Of course, a mattress isn’t considered “tech” necessarily but there’s some really cool companies out there innovating. Just about 10 years ago, the mattress in the box with companies like Casper were just coming out. Nowadays, you have many of these companies offering different cooling features, materials, and firmness.

In another 7-10 years, we’ll likely see the next iteration of the mattress industry. And I’ll probably be back out in the market for yet another mattress.

Monday thoughts

In the latest sign that it’s time for a change, my allergies in San Francisco have been awful and have put me on my ass the last week. Things got better late Saturday a bit as I got out of the city and got to seemingly fresh air away from pollen or whatever else I’m allergic now. I’m now ready for that fresh New York crisp air. I’m convinced the pollution in NY may be better than this pollen air in SF.

The move is picking up quite a bit. Sophia and I made our first big dent into packing over the weekend. I hope to be just about 75% done with packing by Friday afternoon. We have an incredibly busy weekend with seeing friends in town, our goodbye party, and a Sunday wedding celebration. Going into the weekend feeling that we’re almost ready for the movers on Tuesday will put me in a real good spot.

As for the move, I’ve decided to more or less take the next two weeks after this one off to deal with the stress. I’ll still do a bit of work next week, but I hope that the time off will be a nice reset and make the move as easy as possible. The anxiety of everything I need to do hasn’t been easy.

On another note - fatherhood rocks. Colin is a couple weeks away from 6 months and he’s just an amazing kid. I love doing everything with him. Just sitting there watching him explore and play by himself or with me is such a joy. I couldn’t imagine going through life without having children. It’s a void in my life that I really didn’t know I had.

We had a great time over my Dad’s place for Easter. My cousin and sister came into town. Watching my entire extended family including my Dad interact with Colin is an amazing experience. Colin is a star and he loved being the center of attention on Easter Sunday.

Despite all the stress, I can’t wait to get him to New York to show him the city and go on some adventures. In a couple weeks, we’ll hopefully be almost settled in and have New York to explore with some days off. I can’t wait.

IRS cuts

Unfortunately something is in the air here in San Francisco and I’ve been feeling like shit all week. I feel sick, but it seems to be allergy related given my dry cough and that lots of others are also in the same boat. I can deal with a running nose and cough, but the fatigue and brain fog has been really rough on me. It’s not a fun time right now, but hopefully with some rest it’ll pass.

Another tax day has come and gone, and unfortunately this year was a lot more eventful. I just read that the Acting Commissioner of the IRS is stepping down. This is amidst mass layoffs at the agency.

As someone with a tax background, this is a concerning situation happening. I had spoken to a friend who works at a tax API startup, and she mentioned that there’s a sizable percentage difference of people who filed last year compared to this year. The assumption there is that people are waiting to see what happens at the IRS before they file their taxes.

If there is no enforcement, fraud will undoubtedly be rampant. I do not love the IRS and do believe there needs to be major overhauls, but simply firing half the department isn’t good for anyone except the fraudsters. I would understand the decision more if we had gone through a modernization process than eliminated the need for half the IRS, but that is definitely not the case here.

Celebrating how far we've come

One of the hardest parts about running a small business or a startup is the fact that you’re always trying to raise the bar and your success breeds more work in the future.

You have a successful quarter, and then the next quarter is a much bigger goal meaning you’re going to have to work more and harder. You raise a fund which is a major milestone and then you eventually deploy it, and then you have to go out and raise that next fund.

You rarely have the luxury of accomplishing a goal and then being able to relax for an extended period of time. Often times, it’s a one or two week recharge and then you’re back at it. Of course, this is also the reason why building a business is so rewarding.

All that said, I want to make sure that we celebrate how far we’ve come here at Secfi. Sitting in 2022 with the market crashing, things wee not looking great. We had capital so we knew that we weren’t going under imminently, but the private market crash meant that things were about to come to screeching halt on the revenue and fundraising side.

We had to make a ton of tough decisions and really grind through 2022 through 2023 to survive. We did exactly that and then 2024 was the first signs of growth again which was rewarding, but we quickly switched over to 2025 and had more ambitious goals.

It’s easy to forget how far we’ve come since those tough times in 2022. It feels like we haven’t accomplished a lot, but yet we’re sitting here in 2025 in a prime position right now. We successfully navigated the multi-year down market to get the company in a great spot to take advantage of the next cycle. That’s something to celebrate and we need to remember to do just that.

Zoom fatigue

I’m not sure what percent of me feeling tired all day is due to lack of sleep vs. just having a tiring job vs. being alone in an office just on Zoom all day vs. other factors.

I can probably guess that being on Zoom calls all day does not help. If being an “extrovert” means I get my energy from other people - does that same effect still happen on Zoom? I’d probably wager that it’s much less so.

I was exhausted all day at work and then went to an investor dinner, and felt reinvigorated for awhile, until the actual fatigue set in.

I am incredibly excited to get to the office in New York and at least move some of my meetings off Zoom and to in-person. In the meantime, I should try different things like turning your own camera off on Zoom meetings. It won’t be a complete fix but hopefully it helps.

2025 is leaving all of us confused

Like pretty much everyone in this state, we’re all confused by what’s actually happening in the market. With a self-inflicted trade war caused by largely one person who is unpredictable, it’s an incredibly difficult time in business.

We’re fortunate that we live in financial services and we don’t have products to manufacture or import. Those that import goods from China are especially feeling the blunt end of the trade war. I wouldn’t even know where to begin if I worked for one of those companies. I feel especially for the small and medium businesses of the world that are dealing with this crisis in real-time.

Despite not having any products that will have a direct impact of the tariffs, we of course are dealing with the secondary effects in the market. 2025 was supposed the year the IPO cracks open, even if it was just a little. There should have been at least a few IPOs by now if not for Trump’s trade war.

The liquidity in the market is desperately needed and the uncertainty of the months ahead are surely preventing anyone from going public right now. There’s not much we can do at this point.

For us, it’s business as usual with some minor tweaks. We’re continuing to be smart with hiring and growth plans. We’ve put off our hiring at least in the short-term until we can get a bit more clarity on what’s actually going to happen. We’ve adjusted our growth plans down a bit to cater for the uncertainty.

Nearly every person I talk to is in the exact same position. We’re all confused by what is happening and what will happen. I do know that there are still great companies being built right now and that IPOs will come back at some point. We’ll continue to focus on what we know and find the right opportunities.

This is 35

I had an awesome weekend celebrating my long-time friend Mike alongside 7 of our other closest friends. It was his “bachelor” party but it did not feel anything like a bachelor party of the past.

Instead of going to Vegas, or Austin, or Mexico City for a long weekend bender, we all drove a couple hours north to a camping ground with some cabins for just one day and night. While we all had some adult beverages, there were no shots or drinking games. My other friend Mike Cordoba also brought his 5 year old son to hang out.

We spent the morning and early afternoon playing a round of golf. And then spent the late afternoon and evening just playing catch and catching up on life with everyone. We stayed up later than normal and I was the first to tap out at around 1:30am which might be a record for a bachelor party for me.

This is 35 and I’m not disappointed by it. We had a ton of fun just telling old jokes and stories and catching up on where everyone is at. There is nothing like old friends and laughter. And despite not seeing some of these guys in 5+ years, it felt like nothing had changed.

At 7am, all 3 parents woke up before everyone else and sat outside playing wiffle ball with our friend’s son. I couldn’t help but think how much has changed these last 20 years. Even 10 years ago, we’d like be sitting there at 7am still partying from the night before.

While that chapter of our lives are closed, it does get me excited to get older and grow up with these guys. On this Monday, I’m feeling incredibly blessed and grateful for the life I have.