Garry Tan to lead YCombinator into the future, Alloy banks another $52 million, and Wealthfront to stay independent afterall
Stretch Four Insights Volume 35
Future gives me one-on-one training, feedback, and recommendations, and Alex, my trainer, is usually the first person who reaches out to me in the morning to let me know what’s on tap at the gym. Right now, I am getting in shape to run a half-marathon in 2023. So I am on a workout plan that includes strength training and an ever increasing amount of miles each week. Below, you can see my performance in the past thirty days where I hit twenty active days, up three days from the previous thirty days. This month, my goal is to double down and get to 25 active days.
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Happy Saturday,
It has been a few weeks since you all have heard from me. I celebrated my 35th birthday last week in three locations. One locally here in San Francisco at Californios with my lovely wife Whitney. The dinning experience was one of the best we have experienced and it increased my enthusiasm about Michelin Star dining. The next morning, my birthday, I flew to Denver for the Fintech Devcon which is a conference focused on developers building within the fintech ecosystem. It’s hosted by Wade Arnold’s Moov and this was my second year attending. I got to meet some interesting people for the first time including Alex Johnson of Fintech Takes and Tommy Nicholas of Alloy (Alloy featured below). I spent 36 hours at the conference, and the next day I headed down to Houston for a guys weekend.
There is a lot to unpack over the past few weeks, but I will highlight a few things below:
YCombinator tabs Garry Tan as is new leader starting in 2023
Some startup highlights on Alloy and Wealthfront
JR Smith’s Evolution
Let’s dive in.
Quote of the week
How can you buy life insurance when you know someone is going to die? - Howard Marks
Tweet of the Week
YC and Garry Tan
Silicon Valley’s Most Powerful ‘Mafia’ Gets a New Boss
The biggest news this week in startup land is related to Garry Tan being announced as the new President and CEO of YC starting in 2023. Tan is an interesting and well-liked member of the insider network of Silicon Valley. He is also the prototypical Silicon Valley archetype. He went to Stanford, he’s a self-proclaimed nerd and designer and a majority of his circle skews white and asian. Tan participated in YC as a founder in 2008 and was a partner from 2010 until 2015 before launching Initialized Capital with Alexis Ohanian. While Tan made big headlines politically with helping recall Chesa Boudin here locally in San Francisco, he is now stepping in to lead YC through an interesting stage of the institution’s evolution. He seemingly wants to build around the current network of founders that YC counts as alumni to unearth the future billion dollar companies. The big question I have is whether the best of YC is in the past? After producing companies like Dropbox, Airbnb, Stripe, and Instacart it will be interesting to see if Garry can help bring back the energy. As a non-YC founder, when I moved to the Bay in 2017 it was the community to be a part of but it is also fairly selective and skews towards the same archetypes as Tan, generally insiders with backgrounds from other institutions like Stanford and now YC alumni led companies. Fast forward five years and that is simply not the case. Founders have a plethora of options for early stage fundraising, engineering is somewhat commoditized as we know see that the best engineers are available all over the world which YC has tapped into by backing more companies internationally. Additionally, early stage startup advice is fairly commoditized and while Tan has a good Youtube channel that alone will not be enough for YC to remain atop and get the constant deal flow it has in the past.
Startup Corner
Alloy expands their round with another $52 million
While in Denver at the Fintech Devcon event I had the opportunity to meet Tommy Nicholas, the CEO at Alloy. In a nutshell Alloy is a reseller of technology and tools that prevents fraud in online financial services. This week they announced an extension round of fundraising. Alloy operates in an interesting area of fintech. They essentially resell core KYC and identity solutions to financial institutions and fintechs. Their bet is not only that fraud prevention will become a larger opportunity with more and more sophisticated forms of fraud emerging online but that the tools need to be purchased through an experience like Alloy and not just directly from vendors.
Wealthfront is going to be independent after-all
Wealthfront announced that it is no longer being acquired by UBS. This is another interesting decision that could be good for Wealthfront in the long-run. USB ended up investing in the business at north of a billion dollar valuation. Sometimes these situations add energy to companies and can sometimes equate to higher valuations down the road. Visa’s attempted acquisition of Plaid that ended up not happening led to Plaid raising at three times the acquisition price not long after things fell through.
Basketball Corner
JR Smith’s Evolution
I came across an interesting story on J.R. Smith who has essentially did a complete rebrand as a student-athlete by joining the North Carolina A&T Men’s Golf team and studying as a student. JR is notoriously known for his mental lapse in the NBA Finals in 2018. At 36, he understands his basketball career is almost synonymous with that moment but he has essentially rebranded. He credits Ray Allen with inspiring him to evolve and not define himself simply as a a basketball player and he also talks of a unique opportunity to play against Michael Jordan on the golf course.
What’s Next
I am working on Long Four Edition 3 which will focus on the 1:1 coaching apps and tools I use on a day to day basis.
This fall, I will look to experiment with new forms of content through this channel so stay tuned and as always I am always looking for feedback from the subscriber base so please email me at matt@stretchfour.co. I was able to meet a subscriber at the Fintech Devcon in Denver and I love hearing rom this community.
At Moderntax, we have been busy working on V2 of our product. We’ve heard from our current customers and prospects that tax information has value but sometimes the value is in being able to access it without an individual or business owner having to share credentials or upload the information. So we have been heads down building out tools to unlock tax data that is on the internet already. This involves the tax and accounting professionals who work with individuals and businesses as well as intergrations into various public and private databases. If you are interested in learning more about what we are building I would love to chat. If you are interested in being apart of our team or as in investor here are the respective links,
Hiring roles: Chief Architect, Full Stack Ruby/React Engineers, Head of Business Operations
Investing in ModernTax: investing information
Back to the trenches.