Startups only look linear and predictable in hindsight.
At Streamlabs, it took us 25 pivots over 9 years to get acquired for $170M. Stonks has taken 11 pivots in 4.5 years. Time to write it down — not just for others, but for ourselves. Writing is a form of clear thinking (h/t ). Writing also helps process where we’ve been, so we can prepare for whats next.
Stonks — Demo Days (6/2021-1/2023)
It was 2021. All of Silicon Valley was on Clubhouse. I hosted a weekly Shark Tank-style show — founders pitching live to VCs. It took off. We moved to Zoom. $200K was wired after one session. We were onto something.
We built a platform around this called Stonks — Live-streamed Startup Demo Days. Like Twitch and Angellist had a baby.
Investors could 1-click request an intro, sign SAFE docs, pool & wire funds in an SPV, and close the deal all from within the platform. Startup accelerators like Techstars, 500, Snapchat, Draper, Hustle Fund, Plug & Play, Capital Factory, Xoogler and others approached us to ask: could they host their demo days on this platform too?
2022 was our best year — we hosted 157 demo days with 70 different accelerators and facilitated over $100m in investments. One of my favorite moments was Erlich Bachmann from the HBO series Silicon Valley grilling founders as only Erlich Bachmann can.
Then COVID ended. YC and others returned to in-person. Online demo days turned from painkiller to vitamin. Behavior normalization hit other pandemic companies too — Zoom, Peloton, Hopin and others saw their stocks drop 90%+ at this time.
It was time to pivot, or be left with bad dealflow.
Stonks Private / Sandhill Markets (01/23-12/23)
Early in 2023 we built, launched and had some revenue on:
- TurboTax for Angels: a tax software for startup investors that used QSBS and tax-loss harvesting to reduce your tax bill.
- Startup Portfolio AI: Automating the task of collecting founder updates using AI from dozens of startups in your portfolio.
- Hiring Demo Days, Reverse Demo Days.
- SaaS Tooling for Accelerators
- YCombinator for Bootstrapped Founders
These all had some revenue, but ultimately didn’t work — too niche of a market, hard user acq., poor unit economics, or something else. We had however assembled a valuable audience of over 100,000 investors, half of whom were accredited.
Our quantitative testing data showed that these 100,000 investors all wanted to invest in OpenAI, SpaceX, Stripe, Anthropic and other hot late-stage pre-IPO deals. So we built and launched several iterations of Stonks Private / Sandhill Markets:
- Annual Subscriptions for deal access
- Live real-time Auctions (my favorite ❤️)
- Investing on a per-deal basis
One of my favorite moments was organizing a fan sit-in at the Tesla factories in Austin and Fremont to petition Elon Musk to let us invest in his buyout of Twitter. It worked, we got access to the Twitter/X.com deal!
At its peak: $500K ARR. But SpaceX and others sent cease-and-desists. They didn’t want a horde of small checks. We were on the hitlist of General Counsels and legal teams everywhere.
There was a fundamental misalignment of incentives here: successful pre-IPO companies did not want lots of small investors in their deals. But those were the companies that angel investors really wanted to invest in.
In one extreme example, we had a small angel investor with a $10k check blow up a $20 million allocation into OpenAI b/c he didn’t wire funds on time and then complained about being left out. OpenAI canceled the entire $20m deal.
In hindsight, it’s obvious why late-stage startups don’t want to deal with hundreds of small investors. Democratizing investing didn’t work here.
Shoutout to Adam (x2), Olivier, Derek (RIP) and Jonathan here; Sandhill couldn’t have happened without you. It was painful AF, but we had to pivot again.
The Return of the Jedi (1/24-9/24)
We had $10m left from the large seed round we had raised in 2021. I looked at buying interesting tools with PMF — in AI, in SaaS, and creator tools. Buying, then scaling, is an underrated startup tactic for getting to PMF. We reviewed hundreds of deals as e/acc holdings but didn’t close any.
An awesome development during this period was that Murti, my brother and co-founder from Streamlabs & Peanutlabs returned to Stonks. Murti coming back gave me the energy to keep going a bit further; multiple pivots are extremely draining and near-impossible as a solo-founder. Eddy also came back too.
“If you want to go fast, go alone. If you want to go far, go together.”- old Chinese proverb
We both came from the live-streaming world and “Twitch for Investing” was always an idea we had wanted to try. Stonks v3 was launched in summer ’24. It quickly grew to thousands of daily users, and a small, core community started to develop around day-trading stocks. We even got some public-market CEOs to come interview on Stonks!
A live-stream format worked particularly well for stock & crypto day-trading communities. Unfortunately both Murti and I are not day-traders, and we’re pretty opinionated on this subject that day-trading is bad for most people. Studies have shown that 90%+ of day-traders lose money. Twitch for Investing had turned into Twitch for Day-Trading. I didn’t want to be a drug dealer here, promoting something that I believed was fundamentally harmful for retail investors.
Time to pivot.
For the Kids (9/24-5/25)
One night, I was in ChatGPT asking:
“How do I provide for my kids if this fails?”
It suggested Roth IRAs for Kids. We verified this with lawyers and CPAs — it could work if structured correctly. We launched it under the Mora brand.
To do it right, we became an RIA (Registered Investment Advisor). Passed the Series 65. Partnered with Schwab (FDIC/SIPC-insured accounts). Friends, family, and Stonks users loved it. Saving millions for your kids tax-free was worth the struggle.
But new customer acquisition was slow — 6 months and 10+ touchpoints. We still believed. The foundation of tax-savings was solid.
But then Trump introduced the one, big beautiful tax bill. This introduced a new account type specifically for kids with a free $1000 from the government. No complicated lock-ups or eligibility rules like the Roth IRA. Great for the country, but bad for us.
We tested another version of Mora that was more focused on estate-planning, but the CAC/LTV numbers didn’t work as soon as we scaled up marketing spend to anything significant.
We had to pivot again. Shoutout to Kele, Kyle, Jerry, Beth and Suvi for being on this part of the journey with us. Thank you Eddy, Carl, Caden and Cassius for continuing.
The human cost to pivoting is real— our Slack directory looks like a ghostly cemetery with a hundred names in grey (past team members), and only a handful still active. Murti and I are also suffering from chronic stress-related health issues.
Stonks v4 (6/25 — present)
One of the takeaways from Mora is that there is something very compelling to automating tax strategies. People really like keeping more of the money they make legally, vs handing it over to the government.
We spent the 2010-2020 decade in the creator ecosystems of Twitch, Youtube and Facebook. Murti discovered a tax-strategy that was being used by SMBs and consultants today that could easily be tailored for millions of creators.
We also have an unfair advantage here in knowing creators, the platforms, and their daily needs and issues. Lets see if this is the big one.
Murti and I are also collecting all our pivot stories into a book that’s coming out later this year. Tentatively-titled: 3 startups, 40 pivots: How to Not F****** Give Up. Thumbs up or down on the title? If you’d like a free preview copy, hit me up on X (twitter).
Pivoted with love in Palo Alto, CA.