Wednesday, December 18, 2019

Magic Startup Moments

Startups are hard. There are a few moments in every startups life that feel magical and make the grind (at least temporarily) worth it. Magic startup moments include:

Your first customer payment.
It is not a coincidence that so many restaurants have their first $10 bill framed and hung on a wall. Finding someone who wants your product enough to pay for it, and making money from something you built with your own two hands feels good.

Your first magic executive.
As a startup matures, its leadership bench gets built out. Many first-time founders of managers tend to fight delegating to others. Or they promote "smart, junior athletes" to run a function like engineering or sales and watch them flounder (often while thinking the floundering is normal execution). Then, that magic moment happens - you hire a tried and true, excellent executive for a part of the company. Suddenly, great people get hired, the right initiatives are launched, and that area of the company starts to function incredibly well. This is often the moment when founders learn to delegate, and think "I want more people like her".

That special customer thank you.
Many companies change the lives of their customers for the better without realizing it. For mission-centric companies (for example a genomics company) deep, from-the-heart thank you notes from customers may arrive quite early. For other types of companies a thoughtful email or letter will suddenly show up thanking you for helping your customer and for making their lives better. These letters give you an incentive to keep going.

The sale.
The ends of things are often bittersweet. Successfully selling your company and feeling that you finally made it, that your employees have a stable place to work, that you made money for yourself, your family, and your investors, and that you can relax just a little bit, can be a truly magic moment.

The reunion.
Sometimes an employee will reach out to you years after they left your company to thank you for the formative experience they had working for you. Or, a bunch of "old timers" from the company's early days get together to swap stories and discuss what was and the crazy things your company did to ship that product, keep the lights on, or land that partnership.


Startup life:

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Tuesday, October 1, 2019

Fear of Sales

"Our direct sales and customer success efforts are focused on larger organizations who have a greater number of users and teams and have the potential to increase spend over time... We had 575 Paid Customers >$100,000 of ARR as of January 31, 2019, which accounted for approximately 40% of our revenue in fiscal year 2019." 
-From the Slack S1

We have a unique model that combines viral enthusiasm for our platform with a multipronged go-to-market strategy for optimal efficiency... Our sales model allows us to efficiently turn a single non-paying user into a full enterprise deployment. For the fiscal year ended January 31, 2019, 55% of our 344 customers that contributed more than $100,000 of revenue started with at least one free host prior to subscribing. These 344 customers contributed 30% of revenue in the fiscal year ended January 31, 2019. 
-From the Zoom S1

Two of the most viral, bottoms-up products in the history of enterprise software benefit immensely from direct sales[0]. For Slack, 40% of their revenue comes from just 575 customers (out of 88,000 paying customers and 500,000 total customers!) while for Zoom 344 customers generate 30% of their revenue (up from 22% and 25% in the prior two years). Big customers are growing faster for Zoom versus customers overall. I know Slack started on enterprise sales late, so it is possible this number could have been even larger today.

Many technical or product-centric founders have an innate (and inappropriate) fear of sales[0]. While it is inevitable that their company will need to adopt direct sales, technical founders often procrastinate on building a sales force. This is usually a mistake. If direct sales could boost growth from 15% a month to 20% a quarter on $1M in ARR, the company will have $184M in revenue versus $93M in revenue after 4 years[1].

If the company actually does not have good bottoms-up adoption, the impact sales can be even more striking. In DataDog's case, 72% of their ARR is from large enterprises.
We have a highly efficient go-to-market model, which consists of a self-service tier, a high velocity inside sales team, and an enterprise sales force. As of June 30, 2019, we had approximately 8,800 customers... Approximately 590 of our customers as of June 30, 2019 had annual run-rate revenue, or ARR, of $100,000 or more... accounting for approximately 72%of our ARR... Further, as of June 30, 2019, we had 42 customers with ARR of $1.0 million or more" 
- DataDog S1 

So why do product-centric founders fear sales?
1. Familiarity.
Most technical founders have strong familiarity with bottoms-up sales. They download open source packages all the time, and adopted Github or PagerDuty or Stripe through word of mouth. What many founders have not seen directly is how well a repeatable sales engine can work.

The simplest advice to founders on this point is "just do it". Just as you needed to learn how to do PR,  how to hire and negotiate salaries, how to raise money, or how to hire other specific functions (finance, legal, customer support etc, you will need to learn how to do hire sales people and add go-to-market as a function.

To learn how to hire a sales leader, you need to take the same steps you took to learn how to hire marketing or customer support or legal - ask others who are 2-3 years ahead you as founders who have done something similar how they did it. Or go and find 3-5 great sales leaders or CROs and ask them how to hire, and interview for the role, and how to best run the function.

Just as you do not need to run your finance team yourself, you can hire a great sales leader to partner with to drive sales for you.

2. Perception of sales as an art versus science. In reality there is a sales playbook.
Since sales are stereotypically driven by people with liberal arts degrees who played sportsball in college, technical founders often view it as a bit of dark magic involving expensive dinners, cross country flights, and a lot of small talk, high-fiving, and gong-hitting.

In reality, sales is a giant process engineering exercise which has benefited from 40 years of iteration. A great sales leader will have an effective playbook they can apply, a pipeline process to run, and a hiring and compensation approach that will work for your market.

Sales at its best is a repeatable, understandable operational process that can be run in a metric driven way. Indeed, sales productivity is dramatically easier to track and understand versus engineering productivity. Metrics may include revenue productivity per head, payback periods, and funnel or pilot conversion and close.

The temptation of a technical founder is to make sales up as they go along. For your sake, it is best to resist this temptation to re-invent the wheel and to hire someone who knows what they are doing. You will obviously need to work with this individual to set overall objectives, interview the first hires for culture and the like. But you should view sales as an integral part of your startup team - and not something to design yourself from scratch.

3. Cool factor.
Bottoms-up adoption is considered much cooler and more organic than doing inside or direct sales. Your customers are coming to you. How cool is that? Why would you ever lower yourself by going to them and actively engaging them?

The even cooler thing is to build a monster company having enormous impact and a platform you can use to influence the lives of millions and generate the revenue and market cap to affect humanity-level productivity and social change.

If resistance comes from your team versus you, explain to them that your goal as a company is to build something great. To build something at scale, you will need to get big companies to adopt your product (even more people can use it!), that all the companies your employees use and admire actually have sales forces, and that sales at its best can provide insights that would be more challenging to get otherwise (see below)

4. Cultural concerns.
"Sales will be an invasion of fratty liberal arts people and our culture will be ruined! There will be people with nicely pressed shirts making small talk in loud voices while making too much direct eye contact! Don't they realize life is not a staring contest?!?!!!"[2]

Often when I hear about the cultural concerns of working with sales, it is from people who have never worked with sales. The reality is:
a. You will ramp sales headcount slowly at first. Unless you have built a sales org before, it is wise to start small. Add a sales leader. See how it goes. Have her add 1-2 people. See how it goes.
b. Sales tends to be geographically distributed. Direct sales people often work in region since much of their time is on the road. Inside sales teams (who are often phone and email based sales) may be more cost efficient to have in a remote office. The reality is you will eventually be going out of your way to get the sales people together in one spot for offsites and conferences, or to spend time at HQ, versus them taking over your home office. The primary place I have seen sales actually dominate a culture is when you have a remote sales office and then add a handful of engineers and leave the engineers to fend for themselves. Or when you have a sales-centric CEO to begin with, in which case the culture will be sales-centric as expected.

Sales will change your culture, but it is an inevitable change. Instead of fighting it determine how you can productively incorporate sales people. How can you grow in a sustainable manner? How do you want your culture to evolve? Taking it slow is a better long term solution than not doing it at all (or waiting to long and regretting it).

5. Sales at its best.
At its best, sales is not only a large revenue driver, but also a way to get customer feedback and input back to the team. It should drive rapid revenue growth while feeding your team competitive intelligence, customer concerns, feature requests, and other insights from the field. These can help drive business strategy, product roadmaps, and your ultimate success as a company.

6. Sales can cause a company to overspend and crash & burn.
I have seen instances where a company overhires a sales force before it has a repeatable working sales model, or real product-market fit. In this case, a sales team can be existentially bad for a company. You will burn through all your cash before sales shows success. Often this happens when an incoming sales leader over promises and over hires, and sales productivity is slower than expected. For example, a company may hire 20 sales reps and promise a 6 months payback period, when in reality the new sales reps ramp slower and are less productive. Suddenly, the company is stuck paying out a sales guarantee to new hires and it blows up due to poor cash management. This pattern is actually quite common. It is often better to start sales teams small and experimental, and then ramp.

Give yourself permission to ramp sales slowly, make sure things are working, and then ramp some more.

Fundamental Decision
The fundamental decision a technical or product-centric founder faces is this:
Do you want your product to be adopted by as many people as possible, including people working at the largest companies in the world? Do you want to win your market and industry?

If your answer is yes and you are running a SaaS or enterprise company, you should start to build a sales force as soon as you have signs of product market fit[3]. Don't wait. Don't procrastinate. Don't make excuses. Even if bottoms-up is working, you will end up with a smaller, less important company if you wait on building real sales and customer success teams.

You should feel free to start small and take incremental steps - but the key is to take the steps early. Don't wait too long. You may also go through 1-2 sales leaders before finding the right one (and understanding what to look for for your product and culture)[4]. That is OK too. Give yourself permission to make a mistake or two, and let your team know this is all an experiment. This is all about the long term.

Thanks to Stephanie (Schatz) Friedman for early comments on this post.

[0] A quick aside on sales definitions:

[1] You of course want good unit economics and payback times on any customer acquisition efforts, including direct sales.

[2] I am of course joking. I have a technical Ph.D. and a math degree so actually kind of hate most small talk.

[3] Assuming your price point and return on a customer is high enough. For example, if you are only making $100 per year per customer, you can not afford a sales force. At tens of thousands per customer, you can afford an inside sales force. At $100K+ per customer, you can afford direct field sales.

[4] By the way, if your gut is telling you the new sales leader or AE is doing a bad job, they probably are. I have often seen technical or product-centric founders second guess their own judgement on people in these roles. Excellence has the same feel irrespective of function.

Tuesday, June 18, 2019

Industry Towns - Where You Start A Company Matters

Industry towns[1] emerge due to the critical mass of having employees, entrepreneurs, suppliers, business partners, potential customers, and investors in the same geographic location. Some industry towns are driven by their geography - for example manufacturing sites on the Mexican side of the US-Mexico border, Houston for oil & gas, or wineries in Napa (where the right conditions exist for grapes to grow). Other industry towns emerge due to early founding effects - for example Detroit largely emerged as an automotive center as Henry Ford and Ransom Olds happened to live there when they set up shop (Ford Motor Company and Oldsmobile)[2]. Other companies and suppliers moved to be close to Ford and Oldsmobile and an industry town was born.

If you were going into the movie business, you would be encouraged to move to Hollywood, Lagos, or Mumbai. If you wanted to go into finance, New York, London, and Hong Kong would be amongst the primary places to move. Industry towns exist for most major industries, including energy, finance, movies and entertainment and other areas.

Oddly, it is now controversial to say industry towns also hold true for tech - if you want to start a company that will be worth $10 billion or more, the best places to start it are Silicon Valley[6] (for the US), Beijing (China), and Bengaluru (India). There are also regional centers of excellence (Jakarta for Indonesia, Singapore, Sao Paolo for Brazil, etc.) and then secondary centers in the main markets (London, Stockholm, Paris, Berlin in Europe amongst others. Shenzen and Shanghai in China. New York, and to a lesser extent Los Angeles, Seattle, Boston, San Diego, Atlanta, DC and others in the US). This does not mean it is impossible to succeed elsewhere. Rather, startups (and careers) are hard enough as it is, so loading the deck in your favor matters.

On average, being in an industry town is more likely to lead to success than being elsewhere. There will, of course, be successes everywhere. However, market capitalization, revenue, key partnerships, and outsized talent tend to aggregate in industry towns.

Industry towns self-perpetuate as you have a critical mass of talent, suppliers, customers, investors, and know-how in a single geographic area. A cluster, once it exists is self perpetuating and attracts more of the same.

Why Move To An Industry Town?
If you want to go into the movie business and someone told you to go to San Francisco instead of Hollywood, you would think they are nuts. It does not mean that you could not have a movie career in San Francisco - but it would be more challenging[3].  Movies are written by authors who could live anywhere, are filmed onsite around the world, and could be digitally edited from anywhere. Actors could fly to any site in the world to act. But for the Western markets most of the critical mass of the industry still happens in Hollywood.

Technology startups have their own industry towns in places like Silicon Valley, Beijing, and Bengaluru. Secondary towns include London, New York, Shenzen, and Shanghai. On average, going elsewhere will make it harder to succeed in a career in technology.

Similarly, while you can build a technology company from anywhere, there is a real advantage to being in an industry town.

Using the data from CBS Insights on current unicorns, one can quickly see patterns in terms of where private startup market cap is concentrated. I posted a rough quick pass of HQ city data here, for anyone who wants to play around with it, or correct any errors I made. The Europe stat also includes the UK, but the UK is broken out to show its major contribution to Europe. SV = Silicon Valley. I also bundled Bellevue with Seattle, Silicon Valley as a whole, as well as other city suburbs around the world into the city themselves.

The table of raw data:

The table of raw data is below. Last Quarter IPOs for SV are just Uber, Lyft, Pinterest, Zoom as of 6/17/19. You can obviously ignore them if you want to stick to only private companies - I just thought it was notable how much market cap in Silicon Valley just went public.

One can always argue that current market is both a forward looking metric (as investors pay ahead for the best companies) and backwards looking (it takes many years to become a unicorn, so this is a view into where the best companies were being founded 2-10 years ago.

Note that some cities, like San Diego, mainly have unicorn market cap due to biotech. Almost half of New York's market cap is from WeWork, which is more real estate company than technology company - and another $10B or so is from DTC companies (indeed, NY is an industry town for next-gen DTC companies).

Nonetheless, the pattern holds - in every market one city takes most of the market cap. For example, London is 66% of the private unicorn market cap in the UK, Silicon Valley is 57% of US market cap, and Berlin is about half of Germany's.

If you add back the recent IPOs (Uber, Lyft, Pinterest, Zoom) to Silicon Valley, it becomes 65% of total US unicorn market cap.

Here is similar date by overall number of unicorns (versus percentage of market cap):
India is unique in having two cities of roughly equal unicorn market cap with 6 unicorns in Bengaluru and 8 in New Delhi together making up 78% of Indian unicorn market cap.

So why are industry towns so powerful?

1. Talent base. Great engineers, sales people, product people, etc. exist all over the world. However, the highest concentration of outstanding ones are concentrated in industry towns (just as the highest concentration of great actors in the USA live in Los Angeles). Similarly, the people who know how to scale technology companies are concentrated in the tech epicenters in the graphs above. Many companies come to the SF Bay Area to fundraise post product-market fit to access this talent base and know-how.

2. Early customers. For some industries your customers are mainly elsewhere. For example, if you are selling optimization software for oil well extraction, you do not have many customers in Silicon Valley. However, if you are selling generally useful enterprise software or Saas, many early adopters for your product exist in the Bay Area. Technology companies are more likely to early adopt new products than older companies for many categories of enterprise software. Similarly, many early consumer product influencers for technology products are based in the Bay Area[5]. Often, the best place to find early adopters of technology products are in a technology cluster.

3. Unique insights and know-how. What new paid and unpaid channels exist for your business? What are new coding or design trends? Which VCs are funding the NoCode/Devsumer or RPA market? What are the current terms for an M&A offer for a 5-person machine learning team? Industry towns tend to be where early adopters spread insights that an aggressive startup can take advantage of. While some online groups can create similar activity, running into people and serendipity in information spread, board meetings, angel/founder or founder/founder conversations cannot be over appreciated.

4. Smart investors. The best startups in NY, LA, DC, Boston, eventually come to Silicon Valley to fundraise. This is due to a concentration of knowledge, insight, and ambition, as well as dense networks for customers and talent bridged by the investor. Similarly, the best investors in India cluster in Bengaluru and in China in Beijing.

5. Service providers. Legal know-how, banking, and real estate providers with flexible terms or unique outlooks cluster in industry towns. What terms is a specific investor willing to capitulate on? Your lawyer should know. In industry towns they often do.

6. Living and breathing a craft.
Some people are obsessed with their craft. Quentin Tarantino worked as a clerk in a video rental shop and spent his free time watching movies and learning from old masters. The best biologists go to dinner with other biologists and spend all their time talking about biology[4]. Industry towns attract people who view their work and their craft and their hobbies as one thing. Hard work, ambition, and a singular focus are more likely to meet with success than taking it easy, a laissez fair attitude and wanting to do a little bit of everything. While many of the most interesting founders in Silicon Valley are polymathic, they spend the brunt of their time early in their startup journey on their companies and discussing technology trends. Industry towns attract a lot of people self-obsessed with whatever it is they love to work on.

Internet markets are 10X bigger than before. There will be more $1 billion tech companies everywhere.
Online software markets have grown at least 10X in the last 10 years. It has indeed never been easier to start a billion dollar company from anywhere in the world. A company that would have had $10M or $20M in revenue can now reach $100M in revenue due to the global liquidity and reach the internet provides. This means more companies than ever will reach $1 billion in market cap, and there will be more companies distributed around the world than ever before. For example, there are 82 cities in which the 360+ unicorns dwell, and 44 of the cities have only a single company worth $1B or more in them.

In parallel, technology market cap continues to grow most for startups in technology clusters or industry towns. While there are more $1 billion companies all over the world, there are more $10B+ companies in technology clusters. Market cap has historically aggregated to a small number of places. There is no clear "why now" to suggest the effects for industry towns listed above have shifted dramatically enough to displace them.

The rise of distributed teams means that more companies are hiring outside of their HQ city more quickly. If you distribute your team, you need to invest earlier in process. You will need to do goal setting, strong internal communications, and lots of in person meet ups, earlier than most small companies would. Distributed teams have a cost. In some cases the cost may be worth it. In many it is worth waiting until your startup has scale. As tooling becomes stronger we are likely to see even more distribution of teams over time. Over the next 5 years, HQs of the biggest new startups will largely be based in industry towns. 10 years out is always harder to predict.

If you have an advantage in hiring in a local market, you can put your HQ in an industry town and your engineering office in the local market. For example, many Israeli startups will eventually move their HQ to Silicon Valley but keep an engineering team in Herzliya. In some cases, the primary market for talent is the industry town - for example Jakarta seems to attract many of the best or most experienced engineers in Indonesia - so it is not as easy to split the HQ from the rest of the company.

Exceptions that prove the rule
Seattle has spawned two of the most successful companies in tech. Microsoft was originally headquartered in Albuquerque and then moved to Bellevue/Seattle in 1979, and Amazon was started in Seattle in 1994, in part due to its tax rules. Notably, the founders of Microsoft Bill Gates and Paul Allen were born and raised in the Seattle area and then moved back for their startup - just as Ford and Olds created the auto cluster in their hometown of Detroit. While it is likely Seattle will create another mega company some day in the future, its startup scene today is smaller than Silicon Valley, New York, Los Angeles, and other US cities.

Similarly, Warren Buffet is pointed to as an example of how a great finance person does not need to live in NY - since he lives in Omaha. While correct, there are significantly more successful finance people in NY (with spillover now into Connecticut) than there are in Omaha.

I am not arguing that it is impossible to be successful outside of industry towns, but rather there are network and knowledge effects that both pull incredible talent to clusters, and help them succeed faster than they probably would elsewhere. There are always exceptions, but the data on private unicorn market cap above demonstrates the high concentration of the best startups in industry towns.

Some people in tech have a visceral reaction to the suggestion that tech has industry clusters just like any other industry. This is largely driven by their own personal journey "I left the Bay Area for [cityname] and I am doing great in life, therefore this overall thesis is wrong". Or, "I live in [x city] and it is great for my startup." If that is the case, more power to you and congratulations on your success! While great people can be successful anywhere, market cap, venture capital raised, and other data all suggest that industry towns (and their outsized success) are here to stay. As mentioned above, that does not preclude success elsewhere. Technology entrepreneurship is not zero sum.

San Francisco governance - will the tech cluster move elsewhere in the Bay Area?
The city of San Francisco has two potential paths ahead of it. It can create one of the best run, best funded, most progressive and diverse cities on the planet. With an ever growing tax basis, a burgeoning population, and an amazing geographic location, San Francisco should be one of the great cities of the world. Alternatively, a lack of affordable housing, growing homelessness, poor transit infrastructure, and rising open drug use and petty crime can continue to be problems.

The last few years have seen a generational transfer of wealth from pension funds and endowments to San Francisco landlords. Endowments and pension funds back venture capitalists, who fund startups, who hire employees, who give much of their salaries to San Francisco landlords. People who own buildings in San Francisco have made enormous amounts of money while homelessness increases. San Francisco (and indeed, much of California) have building unfriendly regulations that are preventing housing supply from being built where it is direly needed.

It was just 10 years ago in 2008/2009 that few major technology company outside of Saleforce were based in San Francisco. New startups were just moving up to the city or getting founded there. Over the last decade, those startups have grown up into Uber, Airbnb, Lyft, Twitter, Pinterest (which moved from Palo Alto), Stripe (which moved from Palo Alto), Square and others.

From ~1994-2010, most leading Internet companies in the Bay Area were in San Jose, Mountain View, and Palo Alto. From ~2010-today the best new companies have been based in San Francisco. Ten years from now, will we be talking about all the technology startups still in San Francisco? Or will the epicenter have shifted yet again to Oakland, South San Francisco/Burlingame, or another part of the Bay Area instead?

If San Francisco is not able to drop housing costs and the general affordability of living in the city, residents and companies will eventually go elsewhere. While others parts of the area are increasingly expensive, the city in the Bay Area that seizes the initiative on affordable housing, transit, commercial space and infrastructure could become the new tech epicenter of the world.

My hope is San Francisco is able to correct its problems, and that technology companies and employee-residents play their civic role in supporting the city as it transitions.

[1] Also known as "clusters" see for instance
[2] Notably, the automotive industry was considered one form of "high tech" in its day.
[3] For example, Robin Williams lived in the Bay Area for big periods of his life.
[4] And, if single, they may also talk about their dating lives.
[5] There are obvious counter-examples in "middle America" products - like Pinterest & Wish.
[6] I will use "Silicon Valley" and "San Francisco Bay Area" interchangeably in this post.

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Tuesday, May 21, 2019

A Brief Guide To Startup Pivots (4 Types Of Pivots)

Most of the times, startup don't work. At some point it may make sense to either (1) give up on your original product and to sell the company, (2) shut down what you are doing and return money to investors, or (3) to pivot. You can read more on making the decision to give up in a future article. This post focuses on pivoting for small, early stage companies (e.g. 10 or fewer people).

A. The Four Types Of Pivots

1. Pivot inside your existing market, without clear new signal.
The most common type of pivot is to change direction in a market you are already in, but without any new information on the market or a new customer segment. This is the most common type of pivot, and the most likely to end badly. In general founders worry too much about sunk cost and the industry knowledge they have built. So when they pivot, they pivot inside their market instead of considering new areas to work in. In general, startups tend to fail due to bad product/market fit (either the product is not differentiated or needed, or the go-to-market does not work, or both).
"When a great team meets a lousy market, market wins
When a lousy team meets a great market, market wins.
When a great team meets a great market, something special happens." 
- Andy Rachleff, founder of Benchmark Capital
By staying the same bad market, the company may be doomed despite the pivot.

2. Reposition or edit down your product. Find behavior in existing product/market and amplify or focus on that (Instagram, Twitch).
Sometimes your overall product is not being adopted, but some component of it is seeing high use or early signal of user excitement. For example, Burbn was a location check-in app with photos, and the photo portion was getting all the attention so the product was edited down into Instagram.

One could argue Instagram was not really a pivot, but really just good product editing.

Relatedly, the team saw early signal in gaming that led to Twitch being spun out. If your product is seeing enthusiastic adoption in a single userbase or use case, it might make sense to focus all your attention on that use case.

The hard part for most companies in this situation is whether to keep their legacy, non-performing business alive. This is done for both emotional reasons (this was your first product) as well as concerns about market interpretation or branding. There are two ways to deal with this:
A. Launch an entirely new or differently branded product or service (Twitch spinning out of
B. Shut down the original product and focus entirely on the new one (Flickr, which came out of a Stewart Butterfield gaming company[1] or Instagram versus Burbn). If you are pivoting your userbase is tiny, and it will not matter if you shut down.

The downside of keeping the original product alive is the time and attention the product and its customers demand from your team. It may also create a lack of clarity and confusion about your brand and the changes you are making. If your homepage primarily reflects your old product experience your new customers may not engage as deeply. Making a clean break can come by launching a new brand or website or revamping the old one to solely reflect your new direction.

If your legacy business is providing sufficient cash flow to fund a new business it is probably worth keeping and launching a new brand. In other circumstances, you may want to shut it down, sell it, or spin it out. If you really want to give your new direction a shot, you will need to ignore or shut down your prior effort.

2b. Market pivot or product repositioning.
Sometimes it is less about your product, and more about tailoring your marketing and go to market to a different customer base from the one you started with. In many cases this will change the product you build, but sometimes it is as simple as changing your marketing collateral, website, and sales efforts to reflect a new or different customer segment. Are you selling to SMBs but should really sell to big enterprises? Are you selling to consumers but should really be selling to employers?

3. Launch a tool that you used while building your own company (Yammer, Slack).
Some of the most successful pivots (Slack out of Butterfield's second gaming company, or Yammer out of the genealogy site Geni) occurred when a company built an internal tool to run its business, and realized the tool would be valuable to other customers as well. Building something for others, that you need for yourself, is often a successful way to identify a real product or market need. In some of these cases the company is spun out in its own right (Yammer), in others the entire company reconfigures to support the new idea and product direction (Slack). In the case of the spin out, the parent company often maintains some equity portion with the remainder going to a new founding team in the new entity.

In the case of reconfiguring an entire company, the hard part of this sort of pivot is to rebuild the team to be able to build the product or sell into the new market. For example, a consumer team will need to build an enterprise sales and product team from scratch. This may lead to significant employee turnover. If you need to make this transition and do lay offs, do it quickly and be as fair as possible to your employees who supported you in the past.

4. Do something truly new (Twitter, GOAT).
The last form of pivot is the most extreme. In this case you put aside the original product entirely, and start to iterate on new ideas on what to build.

If you are doing a true bottoms-up restart, it is worth seriously considering shutting down the existing company and returning whatever is left of the money raised. Or, selling the company for a small return and starting something again later from scratch. More on this below.

B. When To Shut Down And Restart Versus Pivot
If you are considering doing an entirely new idea from scratch you may also want to restart your company. You should check alignment with your major investors, your co-founders, and your employee on who is on board for this change of direction. In some cases, your cofounders and board (or investors) will be fully supportive and you can get going on the new set of ideas. You may lose employees who no longer believe along the way, but that may be a good thing - you need a core set of true believers to weather the storm. The Grubwithus - > GOAT transition is a good example of a grounds up pivot with the investors and founders all aligned and along for the ride.

In contrast, there may be other times where it makes sense to shut down the company and restart. For example, if the co-founders of the company need to change. Or alternatively, investors no longer want to support the team and its new vision. In this case, it is better to restart the company than to fight how to allocate new equity or with investors who no longer believe.

Often in the case of a restart:
a. The company returns whatever cash is left to its existing investors and shuts down the original company.
b. A new founding team is formed. Sometimes this is the same founders as before, other times it may be a new configuration with equity given to the most important parts of the team. Employees may convert to founders, stay as employees, or decide to leave.
c. The original investors are often offered a major portion of the new company's financing round as a thank you for their original support.
d. The new company goes after its new mission and market.

The podcasting company Odeo went through this process. Ev Williams famously bought out the original investors of the company as Odeo was being shut down. One of Odeo's employees, Jack Dorsey, had come up with an idea for a new social communication product that turned into Twitter. Ev, Jack, and Biz Stone (another employee at Odeo) were considered the founders of the new effort, and the team raised money from both existing investors (some of whom passed on the new company) and new investors. The rest is history.

The benefit of a true restart is it cleans up a lot of potential issues. For example, if existing investors don't believe in the new product direction they have a way to partially cash-out out in an up-front and positive manner.  This gives the founders a clean cap table, rewards investor and employee loyalty, and also allows you to stop working with the people who do not believe anymore.

C. Things To Manage During A Pivot
Pivots are stressful times. If your first product is not working you will need to manage multiple parties to make the transition. Sometimes a pivot will blow up due to ongoing fighting between founders, or with an unruly or angry investor.

Founder conflicts.
The two biggest ways early stage companies die is by running out of money and founder conflicts. During a pivot, the optimal situation is that founders continue to work well together, and if one person is in charge she stays in charge. However, pivots tend to be stressful enough that founder agreements ("you are the final decision maker") may fall apart leading to infighting and an inability to move forward. Often if this happens one of the founders needs to leave.

Employee moral.
During a pivot some employees may rally and do whatever they can to help the company make it through a rough transition. Other employees may become fearful or anxious or lose belief in the company. While you may be able to soothe nerves, it is hard to regain belief. It might be best for all parties if non-believing employees move on to another opportunity if they are no longer pulling for the company. If needed, you may need to do a layoff to conserve cash during a pivot as well as remove unengaged team members.

Investor Unhappiness.
Some investors may get upset of unhappy during a pivot. There are a number of reasons for this. Investors may:
a. Feel misled. If a funding round just happened and the company pivots right after, investors may feel that what they were pitched on and invested is very different from the company they now own part of.

b. Worry about losing money. A junior VC partner may worry they will loose their investment and their career may suffer. An angel may worry about losing their investment (in which case they should not have invested in a startup). Non-bought in, worried people tend to become hard to work with. 

c. May wish the CEO / founders had executed better. Sometimes investors interpret a pivot as the founders being weak. This is usually driven by having a VC who has never started a company and does not understand the reality of a startup. Or the CEO may indeed be weak. Alternatively, the investor may think the new idea or direction is a bad one, and feel trapped along for the ride.

To address investor concerns you should try to bring your investors along on the new direction early in the process. If they drag their feet and are truly unhappy with the new direction, you can propose a restart of the company (see above), a buyout of investors who do not want to be involved anymore, or try to sell the company.

Customer confusion.
If the company does a poor job of shutting down old products or communicating what is happening, the company's customers may be confused about what the company is doing. This is especially bad if new customers are confused and suggests the startup has not made a strong enough break with the past (i.e. changing old website content, creating sub brands, or the like). On average, founders err too often on the side of keeping a legacy product alive in order to save face or for optionality, when in reality they should make the hard decision early to shut it down and move on.

While pivots can be challenging for early stage startups, sometimes they can lead to great outcomes for everyone involved. The key is to manage the various stakeholders (co-founders, employees, investors, customers) through the transition, let go of your legacy past, and focus on creating a bright new company and bright new future.

[1] Honestly, the biggest takeaway on pivoting is that you should back any Stewart Butterfield gaming company, with the hope it eventually pivots. See for instance Slack or Flickr.

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Startup life:

Raising Money

Managing Investors