Cheetah in the Rainforest: 2021 Vintage of Venture

“A firm writing seed checks without specific competence in that stage is like a cheetah in the rainforest. The beast is a wonder of nature that can run at a top speed of 60-70 mph in the African grasslands. But place it in the Amazon rainforests, and all its wondrous capabilities will amount to zilch. It’s just not built for it!”

Most 2021 vintage startups got VC ‘cheetahs’ on their ‘rainforest’ Boards. Surviving the new reality that faces them, will require a cathartic reboot.

Had an interesting conversation with a Bay Area-based founder a few weeks back. His startup is in the high-ACV enterprise space wherein the product is solving an intense and wide-ranging problem that is especially applicable to large companies. He got off the blocks in 2021 with a mid-single digit $Mn pre-seed round by a top-tier VC at the idea stage itself. A start that most founders dream of!

However, now two years down the road, the situation on the company’s Board is far from rosy. The company has gone through tumultuous times that are typical for any 0-to-1 startup. While the founder has kept his chin up during this phase, he is very disillusioned with the VC’s advice, behavior & general stance so far. When he shared some specific examples of this with me, my first reaction above all else was that this firm clearly has little past experience of portfolio management at the seed stage & in particular, what founders need in order to navigate its inherent complexity.

As I started relating this to many other founders I have met this year, a pattern is clearly emerging in the 2021 vintage of startups. Specialist VCs who have mainly invested in the Series A & beyond space in the past, went upstream & wrote massive pre-seed & seed checks with minimal or no traction. They were probably under pressure to deploy or get early dibs on the best teams as later stage valuations were going to stratospheric levels.

Seeing these companies now, after most of them have almost consumed their 24-month runway, I am seeing how the lack of milestone-based capital sequencing & strong stage-firm fit has created many fundamental issues with their core:

1/ Armed with big checks from large AUM firms, founders ignored the scrappy, capital-efficient approach right out of the gate. Instead, they bulked up teams & spent disproportionately on go-to-market even before problem-solution fit. Now in hindsight, they have ended up creating fragile organizations that are at the mercy of the macroeconomy & availability of follow-on capital.

2/ Many of these VC firms have put relatively inexperienced team members on the boards of these companies. My guess is because in their overall AUM game, these types of really early investments are probably considered highly risky “option bets” with low stakes in general & therefore, good learning opportunities for more junior members.

While experience by itself doesn’t make anyone a good or bad VC, pre-seed & seed stages of venture capital demand much more art & judgment in company building from all stakeholders. A firm writing seed checks without specific competence in that stage is like a cheetah in the rainforest. The beast is a wonder of nature that can run at a top speed of 60-70 mph in the African grasslands. But place it in the Amazon rainforests, and all its wondrous capabilities will amount to zilch. It’s just not built for it!

It’s a bit counter-intuitive but in my view, the best VC talent (best = strong fit from a personality & skills perspective) needs to be involved in the earliest stages of company building. There is a reason why YC has a strong moat in that stage, & why while most fresh MBAs can invest & do portfolio management at Series A & growth funds, pre-seed & seed needs artists like Paul Graham & Semil Shah that are few & far between.

One of the things I would like to see coming back into the startup ecosystem foundation post this venture downturn is the importance of “capital staging” – rigorously thinking through how the company should be capitalized at the earliest stages, what kind of investors should be assembled for it, the mindset, approach & time a specific company would need to iterate towards problem-solution fit & eventually, product-market-fit.

I would like to see the return of angels, domain operators & specialist boutique VCs partnering with founders at the earliest stages of venture. We need some version of the Arthur Rock & Ron Conway models but modified for this age. These types of stakeholders in turn, would educate and/ or encourage founders to be scrappy, agile and perseverant during the 0-to-1 stage, supporting them in building the most optimal path to the next base camp.

Closing thoughts specifically for the 2021 vintage startups – while it’s not easy to rewire the foundational DNA of a company, it’s not impossible. While the lesser gritty teams will flame out, I am also seeing founders who are acknowledging both the mistakes of the past as well as the new reality that faces them and are determined to learn & re-invent themselves. Even though as an investor, I am not too excited about the 2021 vintage the way it looks & is behaving right now, I will be more than eager (& rightly so!) to back its re-invented & re-wired v2.0.

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Using the Focus Canvas to Cut Burn

As the fundraising environment continues to get harder in 2023, founders & investors are deep into rationalizing business plans & finding ways to cut burn. The first temptation is to follow what I call an “excel sheet” approach – starting with the largest expense items without enough strategic thinking around the revised set of goals, business constraints in this new environment, what is working well right now, & how capital should be most efficiently allocated going-forward.

As opposed to big companies, startups operate with a finite runway, trying to address significant customer problems that remain unaddressed by large incumbents. This requires constant innovation – essentially doing hard, non-consensus things across the stack, everything from technology & design to customer experience & business model, that incumbents aren’t doing.

While big companies can afford to be relatively unscientific in cutting costs & still tide through tough macros with the help of their existing PMF, startups unfortunately, have no option but to play offense at all times in order to continue innovating & thereby, give themselves a chance to survive & succeed. In financial terms, this implies investing incremental $$ into innovation that drives more revenue (& profit), which is what will ultimately save a startup, not investor cash sitting in the bank.

So how should founders think about playing offense while being capital-constrained? I would like to propose a thinking tool called the Focus Canvas:

  • As a first step, rather than focusing on P&L line items, break down your business into specific buckets. These could include customer segments (eg. Individual, SMB, Enterprise etc.), product lines (eg. shrink-wrapped, custom deployment, pure services etc.), platforms (eg. desktop app, iOS, Android, browser extensions etc.), distribution channels (eg. self-serve, inside sales, direct sales, channel partners etc.), geographies (eg. US, EU, India etc.), teams by function/ type (eg. engg., product, design, sales, marketing, offshore contractors, agencies etc.) & other buckets that are relevant for your business.
  • Arrange all the relevant buckets & their constituent elements on a single page. This is your Focus Canvas.
  • On the top-left corner, list the most updated business goals for this year that all stakeholders in the company have aligned on. These could be things like “hit $1Mn ARR”, “show x% retention”, “start fundraising in Q4” etc.
  • On the top-right corner, list all the business constraints you expect to face this year. These could be things like “12 months runway left”, “only 2 backend engineers”, “sales cycle taking 6+ months to close” etc.
  • Now, as you are looking at this Focus Canvas, try and answer the question “what is working well right now?”*. You need to define “working well” for each bucket as per your specific context, also taking into account the above goals & constraints. It could be driven by one or more of revenue growth, most profitable, highest ROI, generating the most valuable feedback, creating the most differentiation, highest team productivity etc. *Note: this step is well-suited for a team workshop/ brainstorming session.
  • The most important step – for each bucket, put a ✅ in front of the element(s) you believe is your best bet to achieve this year’s business goals while navigating expected constraints. Then, ❌ out all other elements in the bucket. This is where ruthless focus is extremely important for the Canvas to do its job well – ideally, force yourself to ✅ only your #1 focus element. In the case of most startups, that’s probably all you can afford to execute anyway.
  • Finally, take the ✅ element from each bucket & weave them into a simple, 1-2 paragraph Focus Narrative. An example to illustrate this – “In 2023, we will focus on the Enterprise customer segment & offer them the standard product suite with a billable custom deployment services wrapper. The product roadmap will focus on the desktop app. We will double down on the internal sales model for distribution, with founders pitching in for strategic logos. To increase our team’s efficiency, we will significantly reduce contractor headcount & re-allocate them to full-time hires in engineering & internal sales.”

This Focus Canvas now provides a clear & strategic view of opportunities to both cut burn & re-allocate resources, while staying on track to achieve business goals & making progress toward PMF. The Focus Narrative can be used to socialize the going-forward strategy across teams in an easy-to-remember way. If used well (read: with ruthless focus), this approach can help startups in playing offense even in a tough economic environment.

PS: sharing a Focus Canvas template that you can use as a starting point. Feel free to download a copy & modify it as per your requirements.

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Learnings from 100s of YC companies

Heard an excellent conversation between Michael Seibel (CEO of YC) and Patrick O’Shaughnessy (top asset manager, also moonlighting as an amazing podcaster). It had many fundamental insights that would help any founder♟ Sharing my top takeaways here:

#1 Don’t be too “smart” for your own good: there is nothing like that one breakthrough idea that is guaranteed to work 100%. Teams need to be willing to iterate, pivot & execute in new directions all the time 🛶

#2 Launch!!! At the 0-to-1 stage, the most important thing is the ability of a team to build & launch a working product, as fast as possible. You can’t build a company if you don’t launch in the first place 🚀

#3 Startups are all about momentum: teams need to demonstrate forward momentum in whatever time they have spent building the product. The best teams generate rapid momentum to acquire users & fundraise with this tailwind 🏎

#4 What kind of problem is worth solving? a) high frequency⏰, b) high intensity🔦, c) high willingness to pay💵. Overall, founders need to have some special insight into the problem they are setting out to solve💡

#5 Founders essentially take 2 kinds of risk: a) product risk🛠, not sure if people need this product (typically taken by relatively younger founders) and b) execution risk🔨, I know this product is needed but not sure of execution (usually taken by more experienced founders).

#6 Be “real” when coaching founders: be upfront in presenting facts about high failure rates. And that to win, you have to reach out for extraordinary (be 2 standard deviations from average). Also, emphasize the importance of developing tools to manage their emotions & health⚖️

#7 Best way to create leverage during your fundraising process? Acquire users & grow m-o-m. Pitch with real users & data. It’s possible to raise money just on ideas/prototypes, but you will have zero leverage in these discussions. Your goal should be to fundraise with leverage💪🏼

#8 What is Product-Market Fit? It’s like a sledgehammer to your jaw. It’s that month or quarter where you get so many users that it breaks your systems. When the sheer market traction bypasses all your spreadsheet plans & projections. When you have PMF, you WILL know it🚰

To conclude, what I found most intriguing was the importance of “bravery” in founders🧗🏽‍♀️ 2020 has shoved in our faces a plethora of issues we are facing as a species. The need of the hour is a generation of founders that take on problems that are intimidating to solve⭐️

Note: this post first appeared on the Workomo blog here.