• 2019

  • Duolingo Earns $100M in Annual Bookings, Raises $30M from Alphabet

  • Duolingo’s Premium subscription offering, which launched in 2017, has contributed to a meteoric increase in annual bookings. It continues to invest more and more R&D into AI and machine learning to power its tutoring software and growth. Duolingo raised some serious money from Alphabet bringing the total valuation of the charming Pittsburgh startup, to roughly $9 billion:

    Popular language learning app Duolingo has raised $30 million in a series F round of funding from Alphabet’s investment arm CapitalG. […]

    Duolingo claims 30 million users are actively learning languages on its platform, and it has emerged as one of the most downloaded educational apps globally. Since its last funding round more than two years ago, it has more than doubled its employees from 95 to 200 and has opened additional offices in Seattle, New York, and Beijing. It also now claims annual bookings of $100 million after it launched its premium plan in 2017, a significant increase from the $33 million it drew in last year.

    (via VentureBeat)

  • 2018

  • Trailmix Ventures Logo

    Trailmix Ventures

  • Every now and then I come across little organizations doing big things

    Trailmix Ventures seemingly runs a tight ship. What looks like 5 managing partners, and a board of 4 advisors that's pretty impressive:

    • Sheila Marcelo, Founder and CEO of Care.com
    • Adam Grant, Wharton professor, author of Give and Take 
    • Neil Blumenthal, Co-founder and Co-CEO of Warby Parker
    • Helene Hahn Lloyd, Co-Founder and former COO of DreamWorks

    For comparison, the indispensable Y Combinator has at least 100 on staff in total. Size of staff doesn't matter for VC's — at least not anymore. But I think Trailmix's manifesto says it all:

    We are in the middle of a profound cultural sea change. In 2017, eighty percent of consumers participated in the sharing economy; by 2020 nearly half of the American workforce will work independently. Increasingly free of institutions, these consumers are seeking new and innovative ways to care for themselves and others; work and cultivate talent; and infuse their lives with beautiful design and wellness.

    Did you gasp when you read that line too? I know I did, and had to confirm. In reality, 40% of the American workforce will be independent workers by 2020 — but still Trailmix is onto something here:

    What about work? The vast majority of millennials overwork, and yet they care so little about their jobs that most would quit in a hot second if something better came along. Life shouldn’t be this way. We see more than a chance for change. We see an imperative.

    Our terrain:

    We invest in companies focused on sustainable well-being

    We invest in companies that help both workers and entrepreneurs cultivate talent

    We invest in companies that help people design more fulfilling and ecstatic realities 

    We invest in brands focused on consumers identifying with passions and purpose

    We look for the experiences that bind us together and the tastes that set us apart

    This trail, of passion and purpose, is one we are proud to walk.

    What an incredibly healthy refrain from the hyper-growth expectations many VC's have. And, talk about giving a shit. Trailmix's current investment batch includes some really interesting startups:

    • Sphynx (3-in-1 Razor, female beauty products)
    • SupChina (China focused media company, fucking rad)
    • SVRF (A You’veTube for VR of sorts)
    • Herb (Weed focused media company and online retailer)
    • Nautilus Labs (Maritime vessel analytics and data reporter)

    Definitely keeping an eye on Trailmix in the coming years.

  • 2017

  • San Fransisco's Golden Gate Bridge

    How Tiny Might Make The Web A Better Place

  • It’s the year 2000 and The Dot-com Bubble has just arrived. I was 11 years old at the time. I don’t remember it. What I do remember is playing Chess on Yahoo! Games or chatting with friends on AIM. Those were the good ol days.

    However, researching The Dot-com Bubble has been eye-opening. Two major factors catalyzed the conflagration of sell-offs, bankruptcy and failure of so many e-companies (as they were called then). Those startups (as we call them now), were plagued with:

    1. A crazy amount of over-spending. [1]
    2. The stock market crash that followed the 9/11 attacks.

    9/11 was unavoidable for those businesses. But overspending, or burning cash was a very serious problem then — and remains a serious problem now. Snapchat lost almost half a billion dollars in 2016. Uber spent $2.6 billion in 2016 alone. Apple, the prodigal son spent $10 billion on R&D in 2016. The tide is pulling back for some of these VC-backed companies, and there may be a tsunami looming around the corner.

    Enter, the holding company.

    Holding companies reduce the risk for owners. If a financial hardship comes for one of the holdings, it’s unlikely the business will disappear as the corporate group as a whole owns a stake. This is a healthy relationship, and strengthens the bonds between business and consumers.

    Tiny's Homepage

    Recently I came across Tiny. Tiny invests in internet startups, but it also buys businesses into their holdings. If you’re a bootstrapped company, struggling to grow under your own weight, or can scale to level that your VC’s want — Tiny will make you an offer (within 7 days no less).

    Their portfolio is very impressive.

    Dribbble, Crew, Designer News, Need/Want, and Buffer are just a few of their holdings. Tiny won’t flip the business, and they won’t come in and micro-manage team culture. These internet businesses are thriving — each one isn’t an Uber-sized goliath, but they come together in harmony. Each one working as hard as the next, producing a quality cluster of nodes for the web. Each one producing jobs, solving problems and existing through lean years and fat years. Even The Walt Disney Company has an immense amount of holdings and assets, which to say the least… is smart.

    If another (VC catalyzed) bubble is coming, and it most certainly will… I believe most of the businesses (if not all) within Tiny will survive. As overspending becomes more and more entrenched, it’s going to get rough out there. Minimizing the next bubble fallout means taking action.

    Holding companies can make the web a healthier place. Less link rot. Less bullshitery like what happened to Vine. No more dead projects like FFFFOUND, RIP.

    Maybe I’m paranoid, buy if you’re not standing underneath the umbrella of a holding company, I’d be worried about survival.