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A founder’s guide to effectively managing your options pool

By Ram Iyer
Allen Miller Contributor
Allen Miller is a principal at Oak HC/FT based in San Francisco. He invests in early- and growth-stage companies, with a particular focus on fintech.

There’s an old startup adage that goes: Cash is king. I’m not sure that is true anymore.

In today’s cash rich environment, options are more valuable than cash. Founders have many guides on how to raise money, but not enough has been written about how to protect your startup’s option pool. As a founder, recruiting talent is the most important factor for success. In turn, managing your option pool may be the most effective action you can take to ensure you can recruit and retain talent.

That said, managing your option pool is no easy task. However, with some foresight and planning, it’s possible to take advantage of certain tools at your disposal and avoid common pitfalls.

In this piece, I’ll cover:

  • The mechanics of the option pool over multiple funding rounds.
  • Common pitfalls that trip up founders along the way.
  • What you can do to protect your option pool or to correct course if you made mistakes early on.

A minicase study on option pool mechanics

Let’s run through a quick case study that sets the stage before we dive deeper. In this example, there are three equal co-founders who decide to quit their jobs to become startup founders.

Since they know they need to hire talent, the trio gets going with a 10% option pool at inception. They then cobble together enough money across angel, pre-seed and seed rounds (with 25% cumulative dilution across those rounds) to achieve product-market fit (PMF). With PMF in the bag, they raise a Series A, which results in a further 25% dilution.

The easiest way to ensure you don’t run out of options too quickly is simply to start with a bigger pool.

After hiring a few C-suite executives, they are now running low on options. So at the Series B, the company does a 5% option pool top-up pre-money — in addition to giving up 20% in equity related to the new cash injection. When the Series C and D rounds come by with dilutions of 15% and 10%, the company has hit its stride and has an imminent IPO in the works. Success!

For simplicity, I will assume a few things that don’t normally happen but will make illustrating the math here a bit easier:

  1. No investor participates in their pro-rata after their initial investment.
  2. Half the available pool is issued to new hires and/or used for refreshes every round.

Obviously, every situation is unique and your mileage may vary. But this is a close enough proxy to what happens to a lot of startups in practice. Here is what the available option pool will look like over time across rounds:

 

Option pool example

Image Credits: Allen Miller

Note how quickly the pool thins out — especially early on. In the beginning, 10% sounds like a lot, but it’s hard to make the first few hires when you have nothing to show the world and no cash to pay salaries. In addition, early rounds don’t just dilute your equity as a founder, they dilute everyone’s — including your option pool (both allocated and unallocated). By the time the company raises its Series B, the available pool is already less than 1.5%.

Use cohort analysis to drive smarter startup growth

By Ram Iyer
Jonathan Metrick Contributor
Jonathan Metrick is the chief growth officer at Sagard & Portage Ventures, where he helps build some of the world's leading fintech companies.

Cohort analysis is a way of evaluating your business that involves grouping customers into “cohorts” and observing how they behave over time. A commonly used approach is monthly cohort analysis, where customers are grouped by the month they signed up, allowing you to observe how someone who joined in November compares to someone who signed up the month before.

Cohort analysis gives you a multivariable, forward-looking view of your business compared to more simple and static values like averages or totals.

Cohort analysis is flexible and can be used to analyze a variety of performance metrics including revenue, acquisition costs and churn.

Let’s imagine you’re the CMO of the “Bluetooth Coffee Company.” You sell a tech-enabled “coffee composer” that brews coffee, tracks consumption and orders replacement coffee when users are running low. The longer your customers are subscribers, the more money you make. You recently ran a Black Friday feature on a popular deals site and you’re interested to know if you should run it again.

The chart below is a simple analysis you might do to gauge your marketing performance. It shows the total customers added each month, and a clear spike in November following the Black Friday promotion. At first glance, things look good — you brought in more than double the monthly customers in November compared to October.

Marketing campaign results in significant uptick to users added

Image Credits: Sagard & Portage Ventures

But before you rebook the promotion, you should ask if these new Black Friday consumers are as valuable as they seem. Comparing monthly customer percentage is a good way to find out.

Below is a monthly cohort analysis of new customers between September 2020 and February 2021. Like our previous chart, we’ve listed the monthly cohort size, but we’ve also included the customer engagement rate (calculated by dividing daily active users by monthly active users or DAU/MAU for each month (M1 is month 1, M2 is month 2, and so on).

This analysis lets us see how the customer engagement of each monthly cohort compares to the next.

Customer engagement by cohort

Image Credits: Sagard & Portage Ventures

From the figures above, we see that most cohorts have a customer engagement rate in their first month (M1, 42%-46%), meaning 42%-46% of new customers use the coffee composer everyday. The November cohort however has materially lower engagement (M1, 30%), and remains lower in subsequent months (M2, 26%) and (M3, 27%). Interestingly, the customer engagement rate only drops with the November cohort, returning to normal with the December cohort (M1, 45%).

Tribe and Arkam back Jar app to help millions in India start their savings journey

By Manish Singh

Even as hundreds of millions of people in India have a bank account, only a tiny fraction of this population invests in any financial instrument.

Fewer than 30 million people invest in mutual funds or stocks, for instance. In recent years, a handful of startups have made it easier for users — especially the millennials — to invest, but the figure has largely remained stagnant.

Now, an Indian startup believes that it has found the solution to tackle this challenge — and is already seeing good early traction.

Nishchay AG, former director of mobility startup Bounce, and Misbah Ashraf, co-founder of MarsPlay (sold to Foxy), founded Jar earlier this year.

The startup’s eponymous six-month-old Android app enables users to start their savings journey for as little as 1 Indian rupee.

Users on Jar can invest in multiple ways and get started within seconds. The app works with Paytm (PhonePe support is in the works) to set up a recurring payment. (The startup is the first to use UPI 2.0’s recurring payment support.) They can set up any amount between 1 Indian rupee to 500 for daily investments.

The Jar app can also glean users’ text messages and save a tiny amount based on each monetary transaction they do. So, for instance, if a user has spent 31 rupees in a transaction, the Jar app rounds that up to the nearest tenth figure (40, in this case) and saves nine rupees. Users can also manually open the app and spend any amount they wish to invest.

Once users have saved some money in Jar, the app then invests that into digital gold.

The startup is using gold investment because people in the South Asian market already have an immense trust in this asset class.

India has a unique fascination for gold. From rural farmers to urban working class, nearly everyone stashes the yellow metal and flaunts jewelry at weddings.

Indian households are estimated to have a stash of over 25,000 tons of the precious metal whose value today is about half of the country’s nominal GDP. Such is the demand for gold in India that the South Asian nation is also one of the world’s largest importers of this precious metal.

Jar’s Android app (Image Credits: Jar)

“When you’re thinking about bringing the next 500 million people to institutional savings and investments, the onus is on us to educate them on the efficacies of the other instruments that are in the market,” said Nishchay.

“We want to give them the instrument they trust the most, which is gold,” he said. The startup plans to eventually offer several more investment opportunities, he said.

The founders met several years ago when they were exploring if MarsPlay and Bounce could have any synergies. They stayed in touch and, last year during one of their many conversations, realized that neither of them knew much about investments.

“That’s when the dots started to connect,” said Ashraf, drawing stories from his childhood. “I come from a small town in Bihar called Bihar Sharif. During my childhood days, I saw my family deeply troubled with debt because of poor financial decisions and no savings,” he said.

“We both understand what a typical middle class family goes through. Someone who comes from this background never had any means in the past but their aspirations are never-ending. So when you start earning, you immediately start to spend it all,” said Nishchay.

“The market needs products that will help them get started,” he said.

That idea, which is similar to Acorn and Stash’s play in the U.S. market, is beginning to make inroads. The app has already amassed about half a million downloads, the founders said. Investors have taken notice, too.

On Wednesday, Jar announced it has raised $4.5 million from a clutch of high-profile investors, including Arkam Ventures, Tribe Capital, WEH Ventures, and angels including Kunal Shah (founder of CRED), Shaan Puri (formerly with Twitch), Ali Moiz (founder of Stonks), Howard Lindzon (founder of Social Leverage), Vivekananda Hallekere (co-founder of Bounce), Alvin Tse (of Xiaomi) and Kunal Khattar (managing partner at AdvantEdge).

“Over 400 million Indians are about to embrace digital financial services for the first time in their lives. Jar has built an app that is poised to help them — with several intuitive ways including gamification — start their investment journey. We love the speed at which the team has been executing and how fast they are growing each week,” said Arjun Sethi, co-founder of Tribe Capital, in a statement.

Transactions and AUM on the Jar app are surging 350% each month, said Nishchay. The startup plans to broaden its product offerings in the coming days, he said.

6 tips for establishing your startup’s global supply chain

By Ram Iyer
Jeff Morin Contributor
Jeff Morin is the co-founder and CEO of Liteboxer, an at-home fitness company that creates immersive workouts.

Startups are hard work, but the complexities of global supply chains can make running hardware companies especially difficult. Instead of existing within a codebase behind a screen, the key components of your hardware product can be scattered around the world, subject to the volatility of the global economy.

I’ve spent most of my career establishing global supply chains, setting up manufacturing lines for 3D printers, electric bicycles and home fitness equipment on the ground in Mexico, Hungary, Taiwan and China. I’ve learned the hard way that Murphy’s law is a constant companion in the hardware business.

But after more than a decade of work on three different continents, there are a few lessons I’ve learned that will help you avoid unnecessary mistakes.

Expect cost fluctuations, especially in currency and shipping

Shipping physical products is quite different from “shipping” code — you have to pay a considerable amount of money to transport products around the world. Of course, shipping costs become a line item like any other as they get baked into the overall business plan. The issue is that those costs can change monthly — sometimes drastically.

At this time last year, a shipping container from China cost $3,300. Today, it’s almost $18,000 — a more than fivefold increase in 12 months. It’s safe to assume that most 2020 business plans did not account for such a cost increase for a key line item.

Shipping a buggy hardware product can be exponentially costlier than shipping buggy software. Recalls, angry customers, return shipping and other issues can become existential problems.

Similar issues also arise with currency exchange rates. Contract manufacturers often allow you to maintain cost agreements for any fluctuations below 5%, but the dollar has dropped much more than 5% against the yuan compared to a year ago, and hardware companies have been forced to renegotiate their manufacturing contracts.

As exchange rates become less favorable and shipping costs increase, you have two options: Operate with lower margins, or pass along the cost to the end customer. Neither choice is ideal, but both are better than going bankrupt.

The takeaway is that when you set up your business, you need to prepare for these possibilities. That means operating with enough margin to handle increased costs, or with the confidence that your end customer will be able to handle a higher price.

Overorder critical parts

Over the past year, many businesses have lost billions of dollars in market value because they didn’t order enough semiconductors. As the owner of a hardware company, you will encounter similar risks.

The supply for certain components, like computer chips, can be limited, and shortages can arise quickly if demand increases or supply chains get disrupted. It’s your job to analyze potential choke points in your supply chain and create redundancies around them.

How to Prepare for Your Eventual Return to the Office

By Lisa Rabasca Roepe
Whether your company wants you back sooner or later, these tips will help you make the adjustment smoothly.

How to Save Money on Your Digital Subscriptions

By David Nield
You don’t have to be tied down to multiple costly services month after month.

11 Ways to Upgrade Your Wi-Fi and Make Your Internet Faster

By WIRED Staff
There's always something you can do to improve your connection at home.

The pre-pitch: 7 ways to build relationships with VCs

By Ram Iyer
Evan Fisher Contributor
Founder of Unicorn Capital and Minimal Capital, Evan Fisher's pitching and investor strategy has helped startups raise more than $2.5 billion.

Most founders fall into an extremely common trap: Just because you produced outstanding results for the last round of investors doesn’t mean new investors will believe you. This new cohort hasn’t seen that performance firsthand, and they have no reason to trust you yet.

As a founder approaching your next round, it’s common to wonder, “How do I get this new group of investors to trust that I will perform?”

In our experience, founders who fundraise successfully are great at building relationships, and they usually deliver what we call “the pre-pitch.” This is the “we actually aren’t looking for money; we just want to be friends for now” pitch that gets you on an investor’s radar so that when it’s time to raise your next round, they’ll be far more likely to answer the phone because they actually know who you are.

But the concept of the pre-pitch goes deeper than just having potential investors be aware of your existence. Building relationships with potential future investors requires you to think less like a founder and more like a marketer — much of the relationship heavy lifting comes long before it’s time to ask for a capital commitment.

If an investor has made a deal in your space, there’s a good chance they know an earlier-round investor who could potentially be a good fit for you today.

There’s a host of advantages to the pre-pitch approach:

  • Good practice: You’re not asking for money. Instead, you’re offering a sneak peek. Since your relationship-builder pre-pitch doesn’t have millions on the line, you’ll invariably be less anxious, which leads to better relationships. Remember: If it’s not a good fit, who cares?
  • Candid feedback: When you’re not asking for money, you’re more likely to receive honest feedback that you might not get in a high-stakes environment.
  • Set the baseline: You should go over where you’re currently at, why it’s actually not time to raise capital quite yet (the inverse of “Why Now”), and what you still have to accomplish until the time is right.
  • Performance-based trust: Put your performance where your mouth is by showing your potential investor where you are today and what you expect to do in the short term. Later on, you can prove to them that you achieved what you said you would.

7 ways to build relationships with VCs

Now you’re probably wondering, “What the heck do I say to build a good relationship with that next-round investor?” Here are a few notes on how to approach the pre-pitch:

Seek the relationship, not the money

Acknowledge you’re early, but mention that you think it could potentially be a good fit later on. State it up front that you’re seeking a relationship and want to find out if you could eventually be a good fit for one another. Don’t sneak in an ask; let the relationship blossom organically.

Here’s an example: “We’re actually not raising yet, and we’re probably too early for you. But I think this is something you might be very interested in, and thought it made sense to reach out, open up a relationship and see if there might be a fit.”

Don’t waste time

The Poop About Your Gut Health and Personalized Nutrition

By Debby Waldman
Researchers are coming around to the idea that there isn't a one-size-fits-all diet. Some companies are going further to find out what fits you, specifically.

You can’t hack your YC application, but here’s what to avoid

By Ram Iyer
Christopher Morton Contributor
Christopher Morton is COO of Cognito.

The Y Combinator application season is upon us. I have been through YC a couple of times and have reviewed thousands of applications as a volunteer in later years.

Typically, you hear advice focused on ways to improve your YC application so it gets accepted. Here are some tips on what not to do and why so many YC applications get rejected. I’ve also put down some advice about what else to anticipate and take into consideration as you navigate the application process.

In short, don’t overthink your application, and keep it simple and straightforward.

When should I submit my YC application?

When in doubt, read YC’s instructions and answer the question literally. Avoid verbose marketing lingo and keep answers short and concise.

The best applications are often those made at the last minute, because applicants do not overthink their responses and toil over details they think need to be shoved into a question. While I do not recommend submitting applications at the deadline because the system has had issues receiving submissions, you can capture the essence of last-minute submissions by being clear and concise.

Remember that your application should be good enough to get an interview, not win a prize. Go back to work instead of spending more time perfecting an application.

YC experiments frequently. For this batch and the last, there was an early deadline that would give accepted teams access to YC before the batch officially began. Applying early gives you an opportunity to land an interview in the early round and to update your application to be considered in the standard round.

Is it OK to submit my YC application late?

Are B2B SaaS marketers getting it wrong?

By Ram Iyer
Konrad Sanders Contributor
Konrad Sanders is founder, CEO, and content strategist at The Creative Copywriter, a tech-specialist copywriting and content agency.

Which terms come to mind when you think about SaaS?

“Solutions,” “cutting-edge,” “scalable” and “innovative” are just a sample of the overused jargon lurking around every corner of the techverse, with SaaS marketers the world over seemingly singing from the same hymn book.

Sadly for them, new research has proven that such jargon-heavy copy — along with unclear features and benefits — is deterring customers and cutting down conversions. Around 57% of users want to see improvements in the clarity and navigation of websites, suggesting that techspeak and unnecessarily complex UX are turning customers away at the door, according to The SaaS Engine.

That’s not to say SaaS marketers aren’t trying: Seventy percent of those surveyed have been making big adjustments to their websites, and 33% have updated their content. So how and why are they missing the mark?

They say there’s no bigger slave to fashion than someone determined to avoid it, and SaaS marketing is no different. To truly stand out, you need to do thorough competitor analysis.

There are three common blunders that most SaaS marketers make time and again when it comes to clarity and high-converting content:

  1. Not differentiating from competitors.
  2. Not humanizing “tech talk.”
  3. Not tuning their messaging to prospects’ stage of awareness at the appropriate stage of the funnel.

We’re going to unpack what the research suggests and the steps you can take to avoid these common pitfalls.

Blending into the competition

It’s a jungle out there. But while camouflage might be key to surviving in the wild, in the crowded SaaS marketplace, it’s all about standing out. Let’s be honest: How many SaaS homepages have you visited that look the same? How many times have you read about “innovative tech-driven solutions that will revolutionize your workflow”?

The research has found that of those using SaaS at work, 76% are now on more platforms or using existing ones more intensively than last year. And as always, with increased demand comes a boom in competition, so it’s never been more important to stand out. Rather than imitating the same old phrases and copy your competitors are using, it’s time to reach your audience with originality, empathy and striking clarity.

But how do you do that?

Social Media Helped These Chefs Branch Out of the Kitchen

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How to Prepare for a Disaster, Emotionally and Mentally

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To start, forgive yourself and help each other.

You Should Be Using TweetDeck

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Let’s make a deal: A crash course on corporate development

By Richard Dal Porto
Todd Graham Contributor
Todd Graham is vice president at Venrock, a pioneering venture capital firm established in 1969.

Wash, rinse, repeat: A startup is founded, first product ships, customers engage, and then a larger company’s corporate development team sends a blind email requesting to “connect and compare notes.”

If you’re a venture-backed startup, it would be wise to generate a return at some point, which means either get acquired or go public.

If you’re going to get acquired, chances are you’re going to spend a lot of time with corporate development teams. With a hot stock market, mountains of cash and cheap debt floating around, the environment for acquisitions is extremely rich.

And as I’ve been on both sides of these equations, an increasing number of my FriendDA partners have been calling for advice on corporate development mating rituals.

Here are the highlights.

Before my first company was acquired, I believed that every acquisition I’d ever read about was strategic and well thought out. I was blindingly wrong.

You need to take the meeting

Book a 45-minute initial meeting. Give yourself an hour on the calendar, but only burn the full 60 minutes if things are going well. Don’t be overly excited, be a pleaser and or ramble on. Pontificate? Yes, but with precision.

You need to demonstrate a command of the domain you’ve chosen. Also, demonstrate that you’re humble and thoughtful, but never come to the first meeting with a written list of “ways we can work together.” That will smell of desperation.

In the worst-case scenario, you’ll get a few new LinkedIn connections and you’re now a known quantity. The best-case scenario will be a second meeting.

But they’re going to steal my brilliant idea!

No, they aren’t. I hear this a lot and it’s a solid tell that an entrepreneur has never operated within a large enterprise before. That’s fine, as not everyone gets to have an employee ID number with five or six digits.

Big companies manage operational expenses, including salaries and related expenses, pretty tightly. And there frequently aren’t enough experts to go around the moneyball startups for new domains, let alone older enterprises.

So there’s no secret lab with dozens of developers and subject matter experts waiting for a freshly minted MBA to return with their meeting notes and start pilfering your awesomeness. Plus, a key component to many successful startups is go-to-market (GTM), and most larger enterprises don’t have the marketing and sales domain knowledge to sell a stolen product.

They still need you and your team.

A VC shares 5 things no one told you about pitching VCs

By Walter Thompson
Kunal Lunawat Contributor
Kunal Lunawat is the co-founder and managing partner of Agya Ventures, a venture capital firm focused on proptech, travel, hospitality and the future of the built world.

The success of a fundraising process is entirely dependent on how well an entrepreneur can manage it. At this stage, it is important for founders to be honest, straightforward and recognize the value meetings with venture capitalists and investors can bring beyond just the monetary aspect.

Here are five pointers that founders should consider while pitching to venture capitalists:

Be honest and accurate

Raising a venture round is, in a way, a sales process, but any claims that could call into question a founder’s trustworthiness can result in a negative outcome rather than an investment.

As VCs, we cannot overemphasize how important it is that founders are transparent and upfront.

Here are a few select cases of such claims:

  • Overstating traction or revenues, which due diligence brought to light.
  • Concealing material attributes of the founding team — such as a co-founder’s commitment to the company, which at best was part time.
  • Speaking of committed investors who were about to wire money to the company, except they were still at the due diligence stage and eventually decided not to invest.

Investing in early-stage companies is often about making bets on people. As VCs, we cannot overemphasize how important it is that founders are transparent and upfront. It is critical to help establish the initial seeds of trust with a capital partner.

Further, most investors understand that things change — if there are any material shifts during the diligence process, communicating them promptly is an additional signal of maturity and uprightness. This will go a long way during the capital raise and beyond.

Know your BATNA

Founders often enter conversations with venture capitalists with a good handle on their product and the business. However, it’s common for entrepreneurs to falter at the negotiation stage, not knowing what their best alternative to a negotiated agreement (BATNA) is.

We have witnessed founders who mistake initial interest in the venture market for real commitment, and unreasonably hike their valuation, which results in them losing serious investors. We have also seen founders fail to ascribe the value serious VCs bring to the table and consequently hesitate to discount their valuation, only to later realize that the existing cap table lacks firepower.

The best way for founders to uncover their BATNA is to run an efficient process. This requires:

How to establish a health tech startup advisory board

By Annie Siebert
Patrick Frank Contributor
Patrick Frank is the co-founder and COO of PatientPartner, a platform that connects pre-surgical patients with fully recovered patients who went through the same surgery. Frank has worked in consumer technology across industries including retail banking, law, real estate and healthcare.

When you enter the health tech industry as a new startup, an advisory board is a crucial foundational step. A board can guide you through industry-specific nuances, help you make important decisions and prove your legitimacy to investors looking for a strong industry background.

An advisory board will be able to give you strategic insights about both your company and the wider healthcare and technology industries.

In my experience of raising capital, the unpredictable financial situation at the beginning of the pandemic meant we nearly lost our $2 million round, but came through with a committed $250,000, which we used to bring in about $500,000 in revenue.

Something that helped this process was building our advisory board and starting small — we didn’t go for all of healthcare but instead focused on two healthcare verticals. This allowed us to prove our concept, build case studies and win contracts with specific teams in our customers’ companies.

It pays off to stay focused and prove your worth so that your advisory board members can champion you in niche markets, with the potential to expand in the future. For this reason, it’s important to identify the main intention behind your board, and exactly who should be on it.

Who to recruit

Three to five people is an ideal starting point for an advisory board, depending on the size and stage of your company. In health tech, you need more than just the healthcare perspective — you also need the insight of those who have already grown technology companies, perhaps outside of the industry. Our company’s board is an even split of two healthcare and two technology advisers, and, ideally, you want to find a fifth who is well versed in both industries.

It pays off to stay focused and prove your worth so that your advisory board members can champion you in niche markets, with the potential to expand in the future.

An M.D., a Ph.D. from a respected institution or a thought leader in your relevant field of healthcare is the most important asset to an advisory board. These are the highly decorated physicians who have strong connections and act as a reference for their peers.

They provide instant credibility for your company, help you get into the minds of both patients and healthcare providers, and can outline how various health systems work.

Virtual Reality Lets You Travel Anywhere—New or Old

By Rose Afriyie
VR experiences, whether in-person or online, can transport you around the globe—or even to space.

Handhelds Still Aren't Designed for Disabled Gamers

By Grant Stoner
Valve's new Steam Deck looks fantastic—but for players with vision or dexterity difficulties, it's just more of the same challenges.
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