Investing in Day One

DayOne recently announced their $1M Pre-seed funding. I am pleased to participate. Here is the story of how I met the company and why I am VERY excited about what they are bringing to the world.

Day One: Cohort-based education for the new entrepreneurial economy.

The Story

I was on a panel with other venture investors recently when a spontaneous “Shark Tank” pitch session broke out. Being the last panel of the day we didn’t want to drone on about ourselves and asked the audience for a show of hands for anyone with a business idea. About 70% of the audience raised their hands. While a few people were actually fundraising with a deck and a pitch, the vast majority (95%) started with “Well have this idea…” Most were first-time would-be entrepreneurs who had no clue how to vet ideas, test product/market fit, attract a team, build a financial model, or talk to investors. As an investor, I say “No” 99.9% of the time, even to very well-prepared pitches from repeat entrepreneurs. On the panel that day I was 100% “NO” with some variation of “come back when your idea is more baked.” After the 20th “NO” I reminded the audience that 99.9% of ideas don’t become companies and those that do a similar 99.9% do not and should not raise venture capital. Yet the passion of these entrepreneurs stuck with me. Having been in their shoes not knowing how to move forward, I ached for a more helpful answer than “come back later.”

A couple of weeks after the panel, I was catching up with my friend Atin Batra from EdTech investor Twenty Seven Ventures. The universe must have been listening because after I mentioned the panel he said “I am investing in a company solving that problem, Day One.”

I met Co-Founders Andrew Hutton (CEO) and Rahul Brahmphatt (COO) the next week. They started Day One after similar frustration not being able to help 99% of the entrepreneurs they came across as pre-seed investors and venture capital incubator operators. MBA’s are expensive and time-consuming. Traditional venture incubators (YC, Techstars, etc.) are expensive in equity, targeted at those on the venture funding path, require idea validation, and are optimized for repeat founders and graduates of the top 1% schools. They decided to focus on idea validation and entrepreneurial coaching for the 99% they used to say “NO’ to. “If I could create an EdTech product for these entrepreneurs for a couple of thousand dollars, I think there would be a lot of takers,” Andrew told me. So they ate their own dog food and set up a cohort-based learning program with ongoing entrepreneur coaching, Day One. With very little marketing Day One has run three cohorts for over 200 entrepreneurs and has a backlog of applicants. Fellows invest in the Day One program to accelerate the trajectory of their entrepreneurial journey, whether that’s launching a new business or growing to become more entrepreneurial.

Feedback has been amazing, Fellows love it:

“So I joined @DayOneD1, there I met my co-founder Kaylee. Kaylee is a rock star and her product knowledge, operational strength and design background will make our company so much better!”


“I have a lot of friends who are capable of entrepreneurship, just need the community and support to start and carry on. That’s exactly what DayOne is!”


For some DayOne might be the start of a journey that leads through the Venture Capital community (YC, TechStars, venture funding, etc.). For others, it can be the spark that gets them going on a lifestyle business during The Great Resignation. DayOne could be an important addition to the Venture Capital ecosystem, and it DEFINITELY is a great product for the 99% of entrepreneurs left out. That is certainly a mission I support. For a deeper dive, you may also want to listen to this Podcast with CEO.

Why I am Investing

I am a big fan of cohort-based learning, having completed a couple of fellowships with OnDeck, been a mentor at incubators YC, TechStars, and ExpertDojo, and invested in Unlu. I have personally experienced this kind of learning delivering significant value at an order of magnitude lower cost than traditional education. When paired with an ongoing community the power is multiplied. The DayOne founders have built a product out of their personal experience in the market over many years and the initial traction is impressive. I believe there is a huge unserved market in the long tail of entrepreneurship and DayOne has the potential to define and lead in this category.

Trends I am betting on

Entrepreneurship for the other 99%. 6.5M new entrepreneurs every year. It is estimated that over 100M Americans have an interest in entrepreneurship. 53% of GenZ expect to own a business someday while 47% have a side hustle TODAY. 36% of the US workforce were freelancers in 2020 which is expected to grow to >51% by 2027. Most entrepreneurs won’t get and should not seek venture capital financing. Every entrepreneur with an idea deserves an inexpensive, structured way to figure out if there is a “there, there.” DayOne promises to provide this.

The great resignation. The Pandemic seems to have caused a massive rethinking of “What am I doing with my life?” Millions are quitting their jobs every month. Many of them are considering striking out on their own. 70% of the audience at my recent panel had an idea and needed guidance forward. There is huge pent-up entrepreneurship in America. By lowering the cost and increasing access, DayOne promises to help unlock this pent-up demand.

It’s never been easier to be an entrepreneur. It has never been easier to strike out on your own. There is a critical mass of Cloud everything, Freelance sites, social media marketing, business services, and everything you need to run a business. Hackers use no-code platforms to spin up apps on a weekend. Twitter and Instagram can test your product message and conversion for a couple of hundred dollars. Yet it is difficult for new entrepreneurs to find their way through the dizzying array of tools and opportunities. DayOne promises to streamline this.

Why this deal is Incisive

DayOne ranks very highly in key areas of our Meta Themes.

Disruptive innovation creates new markets. There are millions of long-tail entrepreneurs without access to education or support. By applying the proven cohort-based education model to this segment, DayOne’s innovation radically reduces cost and increases access. A new market niche is being created.

Platforms Win. Platforms win because they get more valuable over time as more people connect and use them. DayOne is building a potentially very valuable education platform around entrepreneurship which is already spinning the flywheel as 43% of new members come from referrals by alumni. Unlike one-time education experiences, the ongoing community and coaching promise to drive long-term value for both the entrepreneur and the platform.

Great founders figure it out. The founders are solving a very personal problem for a customer segment they are deeply embedded in. They understand their customer and have delivered delight to them on a shoestring. They have figured out product-market fit and are ready to scale.

Invest only when I can be helpful to the company. I want to be helpful to every entrepreneur I meet. I have wanted a better answer than “come back when the idea is more baked.” With DayOne I now have a better answer and will be directing many founders I meet there for more “baking.”

Invest with other smart people. I have invested with Twenty Seven ventures before and have been impressed with their engagement and support of EdTech entrepreneurs. The list of pre-seed funds and angel investors is top-notch for a company at this stage including Gary Vaynerchuck, Antler Global, and many more. I a very excited to join the party.


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