Teaching how the business works

When we were in the very early startup stages, every hire we made had to know how to do a little bit of everything. For example, we had engineers working on operational items such as KYC checks and contract processing. I even attended product and engineering meetings to help out as needed.

An amazing byproduct of being forced to do everything is that everyone generally knows how the entire business works end to end. Early employees quickly became the “Swiss army knife”.

Naturally, as the company grew, we hired more people to do specific functions and roles within the organization. It’s a by product of the company growing up.

However we’ve come to realize that we’ve grown so fast that we’re starting to specialize a lot more and lose the more well-rounded knowledge around the entire business. We’re hoping to reverse that a bit with more in-depth training around the entire business.

As we onboard new employees, they’ll take stints working in different areas of the business. Everyone will sit in on a sales call. Everyone will look to open an account and process a transaction. Our hope is that this will make employees much more well-rounded across the board and hopefully lead to higher performance due to understanding what makes the business run in each step.

Where has this year gone?

I had a crazy realization today that it’s been pretty much a year and a half since the pandemic started. We’re closer to Christmas 2021 than we are to New Years and this year has flown by. Football season is upon us and quite frankly I am excited for wedding season to be over. I could use a long vacation of doing nothing after all this summer travel.

Onto the markets.

The S&P 500 is up 17.8% and the Nasdaq is at 14.5% YTD. It sure doesn’t feel like a year of gains given everything going on. If you had asked me to guess based on feeling and sentiment, I would’ve thought we’d be in a down year. I suppose after what happened in H2 last year, everything is going to seem calm and slow. The public markets seem to be chugging along despite some fears about the delta variant and another shut down.

On the private market side, valuations are through the roof. Deal activity both in the M&A and VC space is at unprecedented levels. There doesn’t seem to be an end either. Funds are raising more money at again, unprecedented levels. Even Blackstone launched a growth equity arm recently.

It’s the best time to start a business in the history of the world due to VCs willing to pour money into companies. It’ll continue to be a great time to start a business for the foreseeable future given how much ammo these funds are accumulating right now.

I have no idea how it all ends, but hey the roaring 20s are here and let’s hope it lasts awhile.

Here we go again?

I had a great week flying to Chicago for work and then flying straight to Portland for the weekend to attend a good friend’s wedding. It was my first time traveling for work and first wedding I attended this year that was a close friend. I caught up with some old friends for the first time in 2+ years.

It felt like everything was normal again.

That feeling was short lived as today San Francisco announced that we are going back to wearing masks indoors again. I know it’s not the end of the world and I will happily wear a mask indoors to help protect others. I understand the need to protect people, but like many others, I am absolutely fed up by this.

The pandemic can and should be over by now. The fact that it isn’t is extremely frustrating. Those that are vaccinated have to pay the price because of the few that are unwilling to do so.

I know this pandemic will end at some point, but it appears that it’s two steps forward, one step back at this point.

The future of business travel

I traveled for work for the first time in a year and a half. One of our partner companies had a team all-hands in Chicago and invited us to do a presentation. It was an amazing experience and I was stoked for the opportunity to travel again.

We presented an Equity 101 session for stock options and had some great feedback from the crowd afterwards. Since the pandemic started, I’ve done many presentations via Zoom and it just never compares to doing things live in person. I had a lot of fun and I got the chance to meet with a lot of our clients as well.

At the beginning of the pandemic, there were a lot of bold predictions around the future of business travel. Many thought that business travel would be dead forever as we go to fully remote. I don’t believe that. After a year and half of not meeting in person, I’m more convinced than ever that people will still travel for work and do it quite a bit.

I do think there’ll be less travel in some ways. Perhaps flying for a weekly one hour client meeting isn’t going to continue given the effectiveness of Zoom, but now that people and companies are going fully distributed, I imagine that we’re going to start to see a lot more get togethers in cities much more often.

At Secfi, we are starting to hire remote from all over the country, but we will have much more frequent get togethers in San Francisco and New York. I’ve spoken to quite a few companies and it appears that this will become the standard in the future.

The future of college football

I’m a huge college football fan and have been ever since I stepped foot on campus at the University of Washington. Growing up in the Bay Area, there was always the Cal vs Stanford rivalry but college football was never that big. Going to a school like UW that cared so much for their sports teams was an amazing experience and I fell in love with everything college football.

There’s been major news in the college football world the last few weeks.

The Supreme Court ruled that the NCAA can no longer prevent college athletes from getting paid for their likeness. This has been an ongoing debate for years. Colleges, leagues and others have been profiting off college athletes for a long time and none of that money has gone back to the athletes themselves.

While I do believe that athletes should get paid, I unfortunately see this as the beginning of the end for college football. We are now in a world where you can buy athletes legally and the highest bidder will win. For better or worse, this will shift the sport into a world where the universities that have the most money and care the most about football will win. This typically happens in the midwest and the south.

I believe that college football will likely shift to a much more regional sport in which the best athletes will start flocking to the biggest schools in the south and midwest where they just care more about football. West coast teams will not be able to contend. This has been the trend over the last ten years and it will only get worse from here.

We have seen the first ripple effects of this as Texas and Oklahoma have been rumored to be making a bolt for the SEC, leaving behind the Big 12. I suspect that this will be the first domino in conference realignment meaning that more changes will be coming.

The tradition and pageantry of college football unfortunately is likely all but over. Teams will need to realign to focus on maximizing as much money as possible in order to contend. As a major fan of a west coast team, I’m not looking forward to the future of the sport.

Live presentations

I’m finally moved into my apartment and it feels great to be home. I got two rounds of golf in with friends this weekend and caught up with people I haven’t seen in a few months. Unfortunately, my work and wedding travel schedule is going to keep me away from the apartment for much of August and September.

Speaking of business travel, I’m doing my first presentation at an all company meeting in Chicago on Wednesday. It’s been the first presentation that I’ve done live since the start of the pandemic when DoorDash brought us in. I’m incredibly excited to start doing these presentations in person again.

There’s just an element of in-person live presentations that you cannot get from Zoom. Getting everyone’s undivided attention and controlling energy levels is just so much easier. I suspect that there’s going to be a lot more energy and excitement to talk about stock options and taxes than my previous presentations via Zoom. It’s just simply a lot more fun.

I’ll be taking two people from our team with me to do the presentation - one of which I haven’t met in person yet. I miss the camaraderie of business travel and I can’t wait to break bread with my colleagues.

Routine

I’m finally back home in San Francisco after a 3.5 month break. My remote work stint was great in many ways, namely I got to work remote in a foreign country while also seeing a lot of friends in New York. It was an experience that Sophia and I may not have again for awhile.

While I enjoyed our time, I am very excited to be home. While I wouldn’t say there was much disruption from working remote per se, there was a lot of personal things to do that took up a lot of time. I just felt busy for the last 3.5 months and it wasn’t just because of work.

Coming back home to San Francisco allows me to get back in a normal routine of work and play. After a crazy 3.5 months, I’m ready to get to the grind of work and my regular weekend golf sessions with the group. I’m already feeling great after two days back. There’s nothing like home.

Staying alive long enough

Count me as one of the people who thought the Suns were going to gentlemen sweep the Bucks after they went up 2-0. The Suns seemed to be peaking and the Bucks seemed to be plateauing in the first two games. I was expecting a fast and easy series.

Give credit to the Bucks who never gave up and have now taken a 3-2 lead in the series going back to Milwaukee. They fought to stay alive long enough and they’ve now taken a lead.

I couldn’t help but compare this to startups and new companies. Sometimes the biggest challenge in starting a new company is staying alive long enough. Often times, a company just needs to make it long enough to catch enough breaks.

I’ve seen this time and time again in my role at Secfi. Companies that I saw 2-3 years ago that seemed to be struggling have now made it out on the other side of the pandemic as new unicorns or on a path to go public soon. And yes, for many that break was COVID-19.

I wish I could speak openly about some of these stories of companies as they are fascinating business cases. Unfortunately, I’ll have to wait until they go public.

The state of VC money

I haven’t written much about technical or industry related topics lately. I’ve just been so busy with work and life events that once I get to my blog, I just want to zone out and talk about life more. I’m hoping to start writing more about fintech, investing and startups when I get back to San Francisco next week.

One trend that I did want to dive into more detail was company valuations and the changing landscape of VC/angel money. Over the last year and half, we have seen record breaking VC/angel investment in startups. Valuations and amount of capital coming into the startups have increased significantly.

I suspect there’s 3 main reasons for this:

• More demand in the market. There’s more money in the system than ever before due to government monetary policy. Investors are putting this money to work increasing the competition for investment. It’s never been easier to raise a micro-VC fund or become an angel investor.

• Companies are growing larger at much faster rates. Improving tech has made building products and generating revenue easier than ever before. Startups are reaching levels much faster.

• Accelerating trends due to COVID. If there’s one good thing coming out of the pandemic, it’s going to the innovation that stems from COVID accelerated trends. New industries have been born and trends that once were going to take years to take hold are now accelerated to now.

Each of these reasons likely warrants it’s own blog post so I’ll look to touch upon this trend more in future posts. For now, it’s back to catching up on emails from the day.

Roaring 20s

Seems like everyone is in summer mode right now. My Instagram feed is full of friends traveling. A lot of my colleagues are out of office many days this month.

I spent Saturday partying with some old friends. Many of them had been living elsewhere for the pandemic and have since started coming back to New York.

Yesterday, the Euro Championship final between England and Italy was played. Bars were crowded to the brink and there were viewing parties where people were standing shoulder to shoulder.

It’s been glorious to watch everything start going back to normal.

For myself, I have a wedding this weekend and then head back to San Francisco and my new apartment. I’m excited to be back home but also realize that I won’t be home much of July or August to appreciate the new apartment. I’ll be flying to Chicago, Portland, Amsterdam, Seattle, New York and Ann Arbor in the span of a few weeks for both work, weddings, and leisure.

I’m already a bit anxious thinking about the lack of sleep, but my excitement levels are through the roof.

The end of my west coast hours on east coast experiment

I’ve officially thrown in the towel on trying to work west coast hours on the east coast. At the beginning of my 3-4 month trip to the eastern time zone, I decided that I would try to work west coast hours in order to shift work hours to when I am most productive.

I’ve written quite a bit on the struggles of this experiment over the last few months. Unfortunately the end result was just that my work hours expanded from 9am ET to 9pm ET.

I suspect that working west coast hours on the east coast would work best for individuals at companies where everyone is working on west coast time. At Secfi, we have people on both coasts as well as Europe so this was a challenge.

In addition, the challenging nature of a Series A startup just made it really difficult to contain my work hours. Instead of taking mornings off to work out, I found myself reading emails from the minute I woke up.

Of course a lot of this is on myself for setting up boundaries, but I just couldn’t ever make it work to the point of success. I am excited to get back home to San Francisco and start working normalized hours again.

Back to reality

I’ve had a hectic few weeks starting with my vacation and then leading into the 4th of July weekend where I was in Asheville for a wedding. I candidly haven’t had much time to catch up on life and work and it’s been bothering me for the last week or so. I’m back in New York and decided to skip a beach day to go into the office, workout and have a personal day.

I suppose not many would consider going to the office on a “personal” day but I needed it for my psyche as I feel like I’ve been constantly falling behind these past few weeks. I’ll feel really good after a few hours of cranking out work.

I’m in New York for 2 more weeks and then I’ll be flying back home to San Francisco for good. Sophia and I signed a lease just off of Van Ness and we’re excited to be in one place again. There was a moment that we thought we might have continued our excursion and gone somewhere else for the month of August. We were really tempted and almost pulled the trigger on heading to Baja California or coming back to Quintana Roo.

At the end of the day, we decided that it was time to head back to reality. I missed our life and friends/family back in SF. We are just about to move into a brand new office in SF and I am excited about that as well. I have not even met half our new team members in person so I’m excited to do that.

I will say that we may make it an annual tradition to try to do an extended remote work vacation every year now. Being in Mexico was a great experience and we’re excited to try to do it again in the coming year or so.

Asheville

I’m in Asheville, NC for a wedding this weekend. It’s a quaint little hippie town nestled in the south. I have heard of quite a few people moving out here for a lower cost of living as well as a slower pace of life. I can see why they chose Asheville.

The city is surrounded by mountains and there’s green everywhere. There’s outdoor activities galore and microbreweries everywhere.

Crime is seemingly nonexistent compared to other major cities. The people out here really care about creating a great neighborhood and community to live.

It’s fairly interesting when I compare Asheville to San Francisco. My twitter feed is completely filled with people trashing San Francisco for many reasons including crime, homelessness, and corrupt politicians.

They’re not wrong and SF has it’s problems, but I for one am excited to get back home. I just signed a year lease starting in July and I have no plans to move. For all it’s problems, I still love San Francisco.

A place like Asheville is a great place, but it’s just not for me long-term.

Goodbye Mexico

I’m officially back working after a week and a half on vacation. It wasn’t a perfect vacation as there was a lot of work and many things didn’t go according to plan, but I do feel energized again.

The highest of my vacation was definitely scuba diving and getting to spend time with my sister who visited for the week. Scuba diving is a new hobby that I’m really excited to continue in the future. It’s a great excuse to make the short flight to Baja every few months :)

On another note, I’m headed back to the States tomorrow after spending the month in Playa del Carmen. It was a great month overall, but I’m happy to head back. I’ve learned that while I did enjoy my month in a beach/resort town, I’m definitely not a beachtown type of guy. A month of “island life” is probably my maximum.

Playa overall has been great. It’s a tourist town, but not so completely overrun. There’s still plenty of local vibes that I loved. The people are generally great and I did love the laid back atmosphere (cervezas all day!). While seafood forward is where I like to lean, the food and particularly the diversity of the food leaves a lot to be desired.

I have caught the travel bug again though after about a year with no travel. I already want to start planning my next adventure.

For now, I’m headed to Asheville for a wedding this weekend, then heading back to New York for two weeks before finally getting back to San Francisco towards the end of the month. I can’t wait to get back to Asian food in New York. One week away.

Scuba life

We went diving off of Cozumel yesterday. It was our first dive after getting open water certified and it did not disappoint. The water was crystal clear and as calm as I’ve ever seen an ocean.

Underwater life is absolutely fascinating. There’s so many different kinds of creatures on the ocean floor and it’s incredible to see while scuba diving.

I’m a big fan of seafood and admittedly have not been as environmentally conscious as some of my friends have been, but being out in nature and scuba diving has changed the way I view the ocean for the better.

Today, we went to go snorkeling with whale sharks and had a miserable experience. I am not a fan of tour groups, but you have to go with a tour group to do the whale shark viewing. It was an early morning pickup with a nice but irritating tour guide.

Unfortunately, the weather took a turn for the worst and the family in our group were the only ones that were able to dive in and see the sharks. We never saw another shark afterwards. It of course rained on us the entire 2 hour boat ride back and we were stuck in traffic in the minivan on the way home.

12 hours later, we’re back to our apartment drinking beers to forget the day. Tomorrow will be a cenote dive and I’m hoping that it will be the big grand finale to my vacation. I’ve heard amazing things and we won’t be with a tour group so I’m looking forward to it.

Last weekend of vaca

I’m a bit over a week into my vacation and approaching the last weekend. It’s been a great week that has been both eventful and uneventful which is great. There’s been a lot of golf and equal parts lounging around doing nothing.

I golfed Playa Paraiso on Monday and Playa Paraiso on Wednesday. The courses definitely have not gotten easier and there were a lot of lost balls. My driver started coming back towards the end before one too many beers ended up taking over the round.

This upcoming weekend is going to be busy and amazing. We’ll be diving in Cozumel on Friday. Then snorkeling with whale sharks on Saturday. On Sunday, we’ll be diving in a famous cenote.

I’ve been doing an okay job at keeping the work at bay. I’ve largely been focusing on only a few important leads although that has taken up more time and brain than I would have liked.

The work is definitely piling up a bit and I need to make sure to not get too anxious about returning. I’m planning on going in with a positive mindset to be present for the big weekend and aim to get excited about returning.

In the meantime, I plan to go all out in these next few days. Lots of diving, swimming, beaches, massages, and cervezas.

Vacation mode

The odd start to my vacation has gone a lot better over the weekend. The weather has held up and I’ve been doing a lot of activities that helps me get away from the computer and away from work.

Oddly, I am writing this while listening to a work call, but I told myself that this is one call this week that I have to join so I’m happy with that. Compromise.

Words can’t describe how great it is going to bed and waking up not thinking about work but rather what fun activity I’m going to do today. I haven’t had this feeling in at least over a year. My colleagues have done a great job picking up after me and trying to limit my work time and I’m very appreciative for the chance.

Sophia and I got dive certified on Sunday despite a couple tough dives. This week will be about golfing, beaches, cenotes, and eating. This weekend will be full of diving and snorkeling.

I’ve got a full week ahead and I’m beyond excited to continue the vacation.

Positivity

It’s been a less than ideal start to my vacation. We’re in the middle of a summer storm and it’s been raining hard since Sunday. Unfortunately, given we were in Playa, there’s not that much to do when it’s raining cats and dogs. No beaches, no lagoons, no cenotes, no diving.

This has admittedly been difficult as plans have been derailed and we’re finding ourselves hanging out at home much more than we’d have liked. I even thought about just working these next couple of days while we wait out the rain.

I put that out pretty quickly after talking to Sophia. We decided we were going to make the best of it and stay positive. There’s still many different ways to unwind than going to the beach.

It’ll be a different first few days of vacation than I envisioned, but I’m excited and hoping this leads to some other serendipitous experiences.

Lesson from the wise

We’ve been making some all-star hires lately at Secfi. One of those hires is our new VP of Sales an Client Operations. It became evident to me starting last year that we would need to bring in someone who has experience scaling a sales org. It was a long search but we found the right person in Neha. She is smart, experienced and just a great person to have on this leadership team.

It was a difficult hire to make considering I have led this team from the start and I had to make sure that whoever was taking over was going to treat everyone right and actually be that person that could 10x this team. We instantly hit it off from our first time speaking and it was pretty evident early on that she was the right woman for the job.

Meeting with Neha yesterday, one thing I asked her was how it’s possible to go on vacation when you are in a high profile sales/business development role with many important leads. Your clients’ needs don’t go away and there are deadlines that don’t ever work with any sort of vacation time. It’s been a challenge for me this past year. I asked Neha for advice on this.

She mentioned that she has the same problem and her top staff always have the same problem. The reality is that you really can’t sideline your clients. Rather than trying to fight it, she said to embrace it and be okay with working with those important leads on vacation, but pass every other possible task.

It felt really great hearing that from her. I realized that I’m not the only one with this problem and that’s just part of being a leader at a startup. I’ve planned my entire week and half vacation based on her advice.

Odd start to the vacation

Wrapping up my last day of work before I take a week and half off and I got mixed feelings going into it.

I got the travel bug starting Sunday night and yesterday was absolutely miserable. It happens almost every time I go to a place such as Mexico. I had thought I was in the clear though as I made it nearly 2 full weeks without catching it. Fortunately, you can run down to the pharmacy and pick up cipro over the counter here so I was able to more or less squash it in a day.

It’s been absolutely pissing rain here in Playa for the last few days and probably for the next couple days. Not ideal weather to start my vacation, but that’s life. I’ll make the best of it regardless and perhaps use the time to just relax, get caught up on life and enjoy time with friends.

On top of everything, I’ve just got a mountain of work to do. I got some really important deals and unfortunately the timing of this vacation is just brutal with the month end happening. I’ll need to manage it though and make sure I take some time to unplug and only work on certain select tasks.

Regardless, I think it’s going to be great for me to sit time and take time off. Get away from the day to day hustle and focus solely on the super important items and getting back to creativity.