Jack of all trades, but master of one

I’ve interviewed a lot of jacks of all trades, masters of none. The problem is, they can’t do the one thing we need done really well, so we always pass. I’m starting to realize that we’re looking for the Jack (or Jane) of all trades, but master of one. They have at least one function that they focus on and absolutely kick ass at. 

At a startup, employees perform a lot of functions. I think that people oftentimes confuse an employee like that as a jack of all trades, master of none. But in reality, when we hire someone we’re looking for the best candidate for a specific role. In a scenario where both candidates are good at hustling, we’ll always take someone who’s specifically very good at marketing, for example, over someone who’s okay at a lot of things, but not great at any one given thing.

It’s important to ask yourself these questions:

“Who’s going to be the best at growing your userbase? An average marketer or the best marketer you can find?”

“ Who’s going to be part of a marketing team you’re building long term, someone who loves marketing or someone who just likes it?”

“Who’s going to build you the best possible product? A product manager who just dabbles in product, along with everything else, or someone who absolutely loves and kicks ass at it?”

If I were thinking about my career in the startup world, I’d think about the one area in which I could be the best. Would I be a great marketer or a great product person or something else? Then, I’d do the everything I could to be the best at that role. Whenever we interview someone who’s jumped from product, to marketing, to something else, we’re not sure how to think of how they’d fit in our company long term. At a certain point, the Jane of all trades need to focus on something, and when that happens, will she be the best person for that role? Just like most things, focus is really important. If I were getting started in the tech world, I'd think about where I could truly excel and focus on that. 

Great books

Going into a long weekend, I thought I'd share some of the books I've enjoyed reading recently. 

Let me know in the comments if there's anything you'd recommend!

Business / tech books
Zero to One: Notes on Startups, or How to Build the Future

The Score Takes Care of Itself: My Philosophy of Leadership

The 7 Habits of Highly Effective People

High Output Management

The Five Dysfunctions of a Team: A Leadership Fable

Good to Great: Why Some Companies Make the Leap...And Others Don't

Elon Musk: Tesla, SpaceX, and the Quest for a Fantastic Future 

Lean In: Women, Work, and the Will to Lead 

The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers

Other books

43 lessons growing from $0 to $1+ million in revenue, twice

Guest post. Originally posted on The Next Web


I realized the other day that we’ve grown from $0 to $1 million with two separate products (HelloSign and HelloFax). This happened a long time ago, but I was recently reflecting on the lessons.

I found a lot of growth truisms to be false. We’ve learned a lot. Some lessons were painfully won, which is why I may sound strongly opinionated about them. They also may be slanted towards B2B products, but I wouldn’t discount them if you’re not in that space.

Here are our lessons:

1. Charge for your product as soon as possible. Really.

Every founder I talk to has a good reason for not charging for their product and it’s usually a bad reason. I remember office hours with Paul Graham. We explained that we were focusing on product now, but would focus on revenue later. He was confused, that somehow we saw a tradeoff between focusing on product and focusing on growth. Building product should equal growing revenue. People show they value your product by paying for it.

2. Revenue tells you what features to focus on

Charging is a powerful indicator that you’re building something people want. If you’re not charging, you’re likely spending money (development time = money) building features your users don’t really want. People who pay you have opinions about what to build next. Making them happy will lead to more people like them paying you (with this caveat: Don’t build a Galapagos product)


3. Focus on the right customer

YC and Paul Buchheit often say find one user and make her happy. I’d amend that. Find one user in a big market that has the highest LTV, lowest churn, and focus on making her happy. Otherwise, you may be boiling the ocean.

4. ‘You have a distribution problem, not a product problem.’

After one board meeting, our investor said, ‘you have a distribution problem, not a product problem.’ It’s a lot easier to change your message and re-focus on a different target market than completely changing your product. Do that before pivoting or rebuilding your product.

5. “Cheaper and better” doesn’t necessarily lead to higher conversions

Cheaper and better is another truism I found mostly false. Customers often doubt a product is better, because it’s cheaper. Strange, I know. I remember one of the Wufoo founders explaining the notion of being more expensive and better. Plus, if you charge more, you can invest more in product and truly make it better.

In fact, I met one CEO who deliberately priced his product higher than his competitors, just to get them to ask, ‘why’. Then, he’d pitch why his service was better than the competitors. When we split tested our pricing, just being cheaper didn’t lead to higher conversions.

Maybe there’s some scenarios where cheaper and better could make sense, but I think this truism needs to be questioned and perhaps the default truism should be reversed: be more expensive and better.

6. Being too cheap or free can lead to less growth

A woman walks by a branch of US electron

It turns out that distributing to businesses takes money and effort. They don’t just show up. Since we had cheaper plans, we couldn’t afford to reach out to more customers. But, with more expensive plans and a higher LTV, we can spend significantly more to acquire customers.

Being ‘cheaper’ and ‘better’ really just makes it so you can access less people.

7. There isn’t a strong correlation between beautiful design and success (in the early days)

Let me preface this by saying, we love design. I’m a huge fan of design and we’re making a big investment now. I think it’ll help us get to the next level.

I remember meeting with Garry Tan, who is an incredible designer. He mentioned that he hasn’t seen a strong correlation between good design and success of startup companies. So, if you have to choose, pick great user experience, then add great design later.

Conversely, focusing on pixel perfection in the early days may even prevent you from getting the revenue you need.

8. Free plans often make business leads feel uncomfortable

A huge customer wanted to use us for thousands of seats. Instead of being excited by our free plans, they just got confused. We lost them. That was painful. Not paying means that you may not be around forever. Paying money for software signals that they can depend on you for this really important function in the future.

Startups underprice all the time. As a business, we signed up for a $15 / month tool. I would have paid $100 / month for the value it provided. I had an unusual moment, where instead of getting excited about how inexpensive it was, I got nervous about using a key piece of software for only 15 dollars per month.

9. Don’t listen (too much) to your users on pricing

Innovate on your product, not the pricing. We’ve tried all types of innovative pricing models, often driven by our user-base, which have resulted in a lot of custom development. Ironically, when we switched back to industry standard pricing, the plans performed significantly better.

money budget finance

10. $5 / month is too cheap

If you’re a business tool and charge $5 / month, you’re likely leaving a lot of money on the table. Justin Kan said that we were running a charity. He was right. We doubled our prices. See #9.

11. Split test pricing early and often

Two years after launching, we doubled our pricing without an impact on churn or conversion. Since we grandfathered all of those users, we have two years of paid plans that could have been paying us $10 / month versus $5 / month. If we had done this split test earlier, we would have effectively doubled our revenue.

To visualize the impact, imagine a company with 1,000 paid customers:

$5 / month = $5,000 MRR (monthly recurring revenue) and $60,000 in ARR (annual recurring revenue).

$10 / month  = $10,000 MRR and $120,000 in ARR

That could be the difference between succeeding and failing as a company.

12. Try to be profitable, at least once

I often meet with founders who tell me that they’re working on free user growth. I’m going to say something controversial: with rare, rare exceptions, you should never just focus on free user growth at the expense of revenue unless you’ve previously been profitable or run a profitable company. I don’t think most new founders know how to make the optimal tradeoff between free and paid user growth.


I remember having office hours with Emmett Shear. I explained that we were focusing on user growth, at the expense of revenue growth. He asked if our company would be harmed by focusing on revenue for six months? From that moment on, we started one of the biggest revenue ramps we’ve ever had.

If you’re not convinced, you should read this amazing article by Mark Suster on revenue.

13. Your number of paid plans will gets messy, and that’s ok

I remember being reluctant to split test pricing plans, since it’d produce more paid plans to support. Then, we did it. Sure, it’s extra work to support them, but it’s well worth it to double your revenue.

14. Prosumers have higher churn

Yep, and the difference is dramatic.

The only way for prosumers to potentially work is if they have an extremely high frequency activity with your product – something they do so often, they see so much value, that they pay, like Evernote or Dropbox. Plus, there really needs to be a massive number of people that could use your software. However, that type of mass market prosumer software is few and far between.

15. The Dropbox referral page is amazing for Dropbox, but does it work for you?

Dropbox has an amazing referral page, where users can perform actions, like inviting friends, in exchange for free storage. It’s been a big source of growth for them and I’ve seen a lot of other companies try it. Of all of the companies I’ve met, I’ve never heard of it becoming a meaningful source of growth.


16. “I don’t use it enough” or “It’s too expensive” means they’re the wrong customer

Some founders react to this feedback by lowering their prices. That’s typically the wrong thing to do. If someone doesn’t use a product often, she’ll always complain about the price, because she won’t see the value in it.

That just means she’s the wrong customer. Instead, find people that use your software often or fix a bigger pain point. See #3.

17. Startups will probably be your first users and complain the most about pricing

Be careful about listening to them, otherwise you may start developing your product or pricing in unnatural ways, which have nothing to do with the real market. We’ve done that and regretted it.

18. Free users make the most noise, but pay the least

We certainly give the best support possible to our free users, but we take their feature requests with a grain of salt. If you listen too closely, you may take your product in suboptimal directions. Build features for the people that pay you.

19. Month on Month (MoM) growth is key

I can’t emphasize this enough. This is what separates lifestyle businesses and startups (PG: Startups = Growth). Build 20 percent+ MoM growth and you could be the next Dropbox.

20. It takes years to stack revenue

Even with high growth, revenue takes time to grow. Average IPO is 7-13 years. It takes time to stack paid plans every year. But, if you have high MoM growth and minimize churn over time, revenue adds up.

Screen Shot 2015-06-10 at 101459
Image credit: Pando

21. Eventually, you need marketing and sales

The danger of the product CEO is that when you love product, every solution is a product solution. Dropbox is one of the very, very, very few companies where this worked out – a group of MIT grads sitting in a room, building great product and viral loops.

However, in the more common world, word of mouth only gets you so far. Marketing, Sales and BD are what make companies grow. Great product just makes it easier.

I met with someone who buys startup companies at low prices that are running out of money. He then implements very standard tactics to make them grow revenue. None of these things are rocket science. These companies then turn into revenue machines. His impact is immediate and mind-blowing.

It’s unfortunate that the founders missed the chance to drive it themselves. Founders will often wait for a natural lift in growth and will keep changing their product until it gets there – even when changing the product no longer make sense.

22. Small variances in churn can have a massive impact on revenue growth over time

This is the best graph on churn I’ve seen. Small differences in churn has an exponential impact on your MRR over time. See below.

Unless you get control of churn, your growth will eventually stop, since churn will cancel out any new upgrades. It’ll become more and more difficult to replace churned users over time.

Screen Shot 2015-06-10 at 101548
Image credit: dskok

23. Annual plans are amazing. Implement them ASAP.

You offer your users a discount for the year and in exchange, you get approximately 10 months worth of revenue right away (depending on how you discount), rather than one month of revenue each month. That can easily make the difference between being cash flow positive and burning money. It can also reduce churn and many of your customers prefer them. Win, win. Plus, when those renewals hit after one year, your revenue takes a big jump. If I were you, I’d implement annual plans ASAP.

24. Engagement is a leading indicator for revenue

Engagement is flat, but revenue growth steady? That probably won’t last. There’s only so much you can do before paid upgrades decrease.

25. Focus on a limited number of metrics

As much as I love metrics, focus your attention on just a few. I’d pick one revenue growth metric, one churn metric and one engagement metric to start. Then, grow your metrics dashboard over time. When you do, implement this one.

We started out with a metrics setup that was really complex and all we got was a lot of wasted time and an important lesson.

26. For fundraising, revenue growth slides are more powerful than free user growth slides


This may be controversial, but I completely pulled our free user growth slide from our deck and stuck it in the addendum. Investors were way more receptive to our pitch. Free user growth is just a proxy for future revenue. So, if you have revenue, just show that instead.

27. Hone in on ‘deal breaker features’, not feature requests

There’s something powerful about someone saying they won’t sign up unless you have X feature or canceling because you don’t do Y. Anyone can have a feature request. Few people will vote with their feet.

Building those deal breaker features will produce more revenue.

28. Always know your runway

I still meet with founders getting blindsided when they realize they’re almost out of money (Don’t be the startup that accidentally runs out of money). Knowing your runway allows you to make smart decisions about revenue and fundraising, early. Just knowing when you’ll run out of money is healthy, since it guides your daily decisions on revenue.

29. Your free users are for marketing

I remember an experienced CEO explaining to me that free users are just one part of the funnel. She thinks of supporting those free users as part of the marketing budget. They spread the word. They become engaged and upgrade later. But, think of them in that context.


30. Growth is not magic and it isn’t a black box

It’s something companies do or don’t. They do it well or don’t. There are tried and true tactics out there.

I see a lot of almost desperate innovating when it comes to growth. Sure, keep looking for the hacks and viral loops. Maybe you’ll come up with your own equivalent of the Dropbox referral page. But, while you’re doing that, there are a ton of sources of growth that are tried and true over the years. You just have to build those channels: BD, PPC, SEO, channel partners, PR, content, API evangelism, viral and more.

31. Business development can do wonders for revenue, if done right

We learned a lot of business development (BD) lessons, some of them were painful. There are a lot of pitfalls when it comes to doing BD when you’re a startup. But, it can (and has) become a huge source of growth. Here are some of the lessons I talked about at a talk at 500startups.

32. Doing paid advertising can improve your entire funnel

There’s nothing like paying money for advertising to make your entire funnel more disciplined. We changed our onboarding, emails, and pricing, all to make our campaigns profitable. The paid ads were only a minuscule part of our growth. But, the rest of the product hugely benefited from those optimizations.

33. Product market fit

Product market fit = entire team (product, bd, marketing, engineer) focused on one market & killing it, in a predictable way. That’s the end goal.

34. Do post mortems on every release

It’s humbling when you make a big investment on a feature, only to have no one use it or pay for it. Do this once and it completely changes how you think of every feature you build.

35. Customer development != growth

Do customer development to focus on the right users. But, don’t get stuck in customer development / research cycles. Customer development is important, but should have a completely different place in your mind as growth. I see lots of companies stuck in customer development cycles, but as a consequence, these companies might never focus on distribution.

36. All word of mouth growth makes some investors nervous

Word of mouth is nice, but it’s not predictable. You need predictable growth.

37. If you build it, they won’t just come

I’ve seen companies go under, waiting for the users to come. They never came.

38. It’s less stressful when you generate revenue

Startups can be stressful. A lot of people have written about founder depression – it’s a real thing. Sam talks about how founders have a lot of weight on their shoulders. Having revenue can significantly ease that weight.

39. Put together a hypothetical pricing page with a spreadsheet and how it’d look when you fill it out with features

That spreadsheet will help guide product development, since everything is connected to revenue. Put higher value features on the higher plans.

40. Customers don’t price shop as much as you think

Our price, in relation to our competitors, doesn’t come up often. Sometimes we’re more expensive, yet we might still win the deal. So, don’t become too obsessed with your competitor’s prices. Just optimize for your users.

41. If you’re only winning on price, rethink the value you add

Unless you’re Amazon, a price war can be brutal. Instead of being cheaper, think about how to differentiate.

price tags

42. Consumers and businesses behave differently when it comes to money

As a company, we pay a huge amount of money for software and don’t flinch, but in my personal life, I’m still on a free Spotify account. Many founders don’t have real work experience before starting a company, myself included. Without being in a work environment, it’s hard for a founder can imagine how much companies pay for software, which leads to underpricing their product.

43. If you’re a SaaS product, read this post over and over again

This is easily the best SaaS analytics post I’ve read

Revenue isn’t a bad thing. Want to know what we do with revenue? We support a team of terrific people that help us build and support this product. Every day we make the product better, because we have revenue. The more revenue you have, the better you can make your product for your customers.

For some reason, the mental default for founders is that their product should be free – and charging needs to be justified. The inverse should be true – the mental default should be that your product should be paid and being free should be justified.

In fact, most pricing truisms should be reversed. Statements like “cheaper and better” should need to be justified, instead of spoken and accepted as truth.

Today is a good day to grow revenue! No reason to wait. I find it weird that I meet with founders and have to convince them that growing revenue is important. Then, runway decreases, they can’t raise, the game is over and everyone acts surprised. (Don’t be the startup that accidentally runs out of money)

In fact, if you this figured out, you may get to the mythical, ‘infinite runway’. Then, if you want, you can turn on the spigot and operate at a loss in exchange for revenue growth. That’s the moment increasing your burn rate for growth makes sense, but rarely before.

Focus on specifics when interviewing

Years ago, I was interviewing a marketing candidate. I asked general questions about how she could meet certain growth goals and she talked about the marketing campaigns she would put in place for us, like SEO, social, PPC and more. 

After the meeting, I thought over whether she'd be a good fit. I realized that I had absolutely no idea how well she'd perform. The things I learned were too generic and nebulous to evaluate.

Anyone can suggest SEO, PPC, PR or any of a dozen other marketing strategies. Plus, it turns out that if you ask if someone can do something, 95% of the time they’ll say yes, which is very unhelpful in assessing a candidate.

Now I focus the vast majority of every interview asking about what people have done, rather than what they could do. What’s the best campaign you’ve launched? Was it successful? What metrics did you track? Did you make any mistakes? If so, what were they? What was your biggest management challenge? Then, I do a deep dive into each of these areas and try to understand what they did and how they interacted with others. I found that the great candidates really enjoy these deep dives, since it gives them an opportunity to really show their skill set and experience.

These answers will tell you how the candidates operate in real life. As soon as I started focusing on their past details, I got a better sense of who they were as a candidate and whether they’d be a great fit.

The less experienced you are as a founder, the faster you should launch

I remember office hours with Paul Graham in 2011, when we were giving yet another excuse for waiting to launch. We wanted to build x,y and z features before launching. Paul Graham advised - 

“Launch when you have a quantum of utility”

We launched and it was the best decision we made. Instead of building what we thought users wanted, we could talk to our users and ask what they wanted.

There’s a tendency of new founders to wait almost indefinitely before launching. I’m always surprised when I meet with these type of founders. Everyone has heard that you should launch fast, yet the founders I meet always have a reason why it doesn’t apply to them.

There's a company I used to know that went months and months without launching. It seems like everyone knows a company like this.

One month becomes two, then three, then four and still no launch. It makes me nervous. I wondered, what are you working on that absolutely needs to be built before launch? When I hear the features that they absolutely need before launch - none of them seem like show stoppers.

They were wasting money and time - the scarcest resources as a startup - on something they didn’t know their users needed. The more time that passes before you have a live product and you're talking to customers, the more likely you're building something you think your users want, versus what they actually want.

When I think of the massive lists of features that founders have to build pre-launch - I always have this image of the Coyote running on air. Last minute, he looks down and realizes he’s not standing on anything and falls. These founders have never launched a product before, so it isn’t their entrepreneurial experience that is telling them to wait. 

I thought of a new rule. The less experienced you are as a founder, the faster you should launch. Or, listen to PG’s advice and launch when you have a quantum of utility.

Seed Rounds: How To Pick A Valuation

I can’t tell you how many times I’ve had this conversation. A founder is about to raise their first round and asking me how to value their company. [1]

There’s a reason it’s so difficult to figure out - valuations have little basis in reality for early stage companies. You evaluate the team, product, market and other variables - then, make a general guess.

Before I go on, if you read nothing else, read this:

Your #1 goals is to get your company funded, so you can build a big business. Funding lets you invest in growing your company faster than revenue growth would normally allow. Do what you can to get your company funded and get back to work generating value.

Here are some ways to value your company:

1. Market size

A big market determines the upside potential. In a world where only the 1000x companies make back portfolios, this is really important. [2]  This can often justify a higher valuations - and for good reason. For some investors, this is the most important attribute and they won’t invest unless it’s a huge market.

2. Revenue

Revenue is how traditional businesses get valued. Early stage companies often don’t have revenue or have revenue so low, it’s not a real indicator of future potential. Companies like Facebook and Twitter didn’t figure out revenue for a long time. This is the main reason the process of picking a valuation can feel so ambiguous. With that said, if you have revenue, this is something you should emphasize.

3. Month on month (MoM) growth

To become a big company, you need high MoM growth for years (PG: Startups = Growth). 20% MoM growth is the gold standard - the longer and more consistent you hit high MoM growth, the better. Even a product an investor doesn’t fully understand - for example, an app that self-destructs the photos it shares - starts to look really good with high MoM growth. This works for revenue or active users.

4. Active users

Free, engaged users are a proxy for revenue, as long as you understand when a free user is valuable and when it isn’t. The threshold is generally higher for consumer startups (Ten million users is the new one million). Moreover, the engagement of your paid users are also important, even though they’re paying you, since it’s a leading indicator of churn.

5. Team

Everyone talks about the Stanford / MIT teams. It certainly can help boost a valuation, but isn’t necessary. Domain expertise can also help.

6. Valuations of other companies like you

Relationally, you can compare your valuation to other companies on Angellist, Y Combinator, 500 Startups or elsewhere.

7. Acquisitions of other companies like you

This is helpful in determining a valuation, since it shows real liquidity for what companies will pay for a company like you, instead of what an investor will pay to invest.

8. Raising momentum / high demand

This method of valuing a company is further from reality than most attributes. If your company is in high demand, it drives the potential valuation up. Hopefully, it’s in high demand for good reasons, otherwise you risk a down round in the future.

9. Accelerator

Being part of an accelerator can help your valuation, since you’ve at least been partially vetted, which decreases some, but definitely not all, of the risk.

Things to note about valuation:

1. Your outcome will likely be binary

I spoke to a YC class about fundraising a few years ago and I still believe this - I’d rather raise $1m at a lower cap than $100k at a higher cap. The former will get us to the next stage as a company. The latter won’t be enough money to grow and without the capital to grow, could risk failing or a down round.

2. The valuation only exists if investors validate it

Traditionally, there’s a lead investor that validates a valuation, but a lot of companies now raise without a lead. By getting a few investors to buy in at a specific valuation, they’re effectively validating the amount. Either way, your valuation doesn’t truly exist until it’s validated.

3. Don’t risk a down round

A down round happens when the valuation of your next round is less than your current round. No one comes away from that undamaged. That can happen when people are too aggressive about their valuation in that first round. Don’t let that be you.

4. Terms often matter more than the valuation

For a higher valuation, you may be giving up some control, like a board seat. I’ve also seen people raise on 2x+ pro-rata, which means that the investor has the option of doubling their stake in the following round, which I think is generally a bad idea. I’d keep your terms as clean and standard as possible. [3]

5. Valuation pride

Why do people push super high valuations? It’s one of the few moments in your company’s history where you can get a stamp of validation. Just like good grades or good schools help drive your self-worth, a great valuation can do that too. It’s something you can tell others or use to compare. So, the bigger the stamp, the more likely you’re seemingly doing well. Don’t be tempted by this.

6. Map out multiple stages of financing

Take a moment and project out your equity over multiple rounds of financing. You need to make sure there’s enough equity to sell, while keeping enough equity for the founders and team. I hear of companies that sell 50% of their company for a few hundred thousands dollars. That won’t leave enough equity to sell for future financing rounds. (The Benefits of Building a Company in the Bay Area)

7. Drive for a ‘fair’ valuation

That probably depends a lot per company, but I kept that word in my head as I figured everything out.  

8. Make sure your valuation doesn’t exclude great investors

Even though it’s hard to know an investor’s value add in advance, make sure you’re not picking a valuation that prevents great investors from investing (Investors and advisors: the crowd, the ringside, and your corner). Note, if it’s a great company, not all great investors will walk away from a high valuation (Sam Altman: Upside risk).

9. Be nice

Invariably, you’ll run into investors that think your valuation is too high. The only right behavior is to be consistently nice and explain your thought process (Treat investors well when fundraising).

10. Valuation versus percentage ownership

Some investors are more interested in the percentage of the company they own, versus the valuation. In that way, you might end up with a higher valuation than you would have had otherwise. You can certainly take this approach to picking a valuation, but just make sure you’ll be able to at least grow into that valuation - preferably grow significantly past it - by the time you raise your next round.

You’ve probably noticed at this point that there’s no clean formula. Even though it’s inexact, investors will want to know the thought process behind the valuation you pick.

Certainly, there are bad valuations, but there’s a larger range of gradations of good valuations and I wouldn’t stress about small differences between the gradations in the good range.

Good luck figuring this out. The key is to not spend too much time thinking about it. Some incredible companies, like Dropbox and Airbnb, got valuations that would seem extremely low in this market for their first rounds.

In the end, it’s your ability to execute that will turn your company into a big one - not your valuation. It’s more important to close the round, get the money in the bank and get back to building.

Would love to hear what you’ve learned about valuing early stage companies in the comments.

[1] This is mainly about your first round. I think a lot of the lessons can apply to later rounds though.

[2] Articles on needing the companies with 1000x returns to justify your portfolio:
Black swans
Upside risk

[3] YC has standard docs you can use. 

Photo credit

This email may be worth millions of dollars in sales

We were comparing two SaaS applications. One gave us a better quote, so we asked the second if they would match it. They wouldn’t, but their founder, wrote us an email explaining: 

  • Why their software is better
  • How their software would save us a lot of money and time 
After reading it, we immediately picked the more expensive choice.  I thought the email was so compelling that I wanted to share it as a great example of how to position a product for value vs. cost.  I've anonymized the company: 

Subject: Re: demo follow up

No worries...  short answer is no, we aren't able to compete on price against FooCorp.

The FooCorps's of the world have spent a couple decades now in a the race to the bottom and it shows.  I have no doubt you can get their product (or a whole raft of others) for a few bucks cheaper than us.

Our product, Acme, is different.  We're designed to help improve your'e company's performance in the critical area of XYZ.  The ROI on doing that is enormous.  

Now, not every organization sees the value in investing in XYZ.  I get that.  But if yours does, Acme is one of the most leveraged investments you can make.

Assume HelloSign does 5-6 transactions in the [XYZ field], that's going to run 300-600k per year (so figure this is a $1-2MM investment over 3 years).  The value of each transaction will be maybe 2-5x that if they're done well, whereas a bad one we know can actually destroy value.

On the cost side, great transactions churn over at less than half the rate of low performing ones - which means if you do a better job at XYZ,  you'll save 10's of thousands in new transaction costs as they stay longer.  And on and on....  

So ultimately if you think Acme will help you do this better - even just a little bit - the whole thing is peanuts.  The cost difference between our product and the others, even less.  

Look, FooCorp's customers are switching to Acme in droves because we're investing heavily in great customer service and innovation.  Those things cost money but, as we see above, they drive tons of value so the market is happy to pay.  

We'd love to have HelloSign on board as a customer and I'd be happy to have another chat with you or them if you think it would be useful.  Let me know!

Acme CEO

The point is, instead of doing a price cut, it may be worth explaining why your product is worth more. This email will probably be worth millions of dollars over the lifetime of their company. 

Either way, he was right. The minor different in price was worth it. The product is amazing.

The Benefits of Building a Company in the Bay Area

move your tech startup to the Bay Area

In 2010, I moved myself and the company from Minnesota to San Francisco. There’s no way we would have been able to build HelloSign in Minnesota.

Every week or so, I hear about a new city that’s trying to become the ‘next Silicon Valley’ or someone explaining to me that Minnesota is a great place to build a tech company.

You certainly can create a good company anywhere. You can also sprint at 20,000 feet. It’s just significantly harder and you’ll be giving yourself a handicap.

If you'd like to see this topic discussed at SXSW Interactive, vote for the panel in the SXSW panel picker. 

Here are seven reasons I moved:

1. Capital

There is a unique ecosystem of angel investors and venture capitalists in the Bay Area. It’s unparalleled for tech companies anywhere in the world.

Over the past 40+ years, the large exits and IPOs (Facebook, Google, Yahoo, eBay and more) have fueled and justified the next funds at VC firms. And they've produced a new batch of rich individuals who’ve become angel investors.

It’s this group’s unique understanding and affinity for tech that has helped produce incredible returns on investments -- which in turn has justified more capital entering the ecosystem -- which have in turn funded more great companies and so on.

We raised capital in the Bay Area in 2011. While we were fundraising and bloggers were calling the environment ‘frothy,’ the Minnesota Star Tribune wrote a long article about how angel investors in Minnesota were cutting back. These are two very different worlds.

2. High concentration of specialized knowledge

Knowledge is almost just as valuable as capital. Within walking distance of our office, you can talk to the people who built Twitter from the ground up and experts on viral growth. Want to learn about SaaS metrics? Reach out to the companies that set the SaaS standard -- like Dropbox, Box, Evernote and others. Even with their level of success, these people are remarkably open and accessible.

3. Culture of risk

My cofounder quit his full-time job at Tripit to take a risk building this company. In Minnesota, I’d be hard pressed to get anyone to quit their job to join a risky startup. Since there’s a lack of capital in Minnesota, starting a company is significantly harder for anyone with a family or any other life expenses.

3. Valuations

Valuations are significantly better in the Bay Area. Since there is a super high concentration of billion dollar tech companies, the returns justify the higher valuations. As one investor explained to me, it’s the Facebooks, Googles and Dropboxes of the world that make this possible.

Moreover, there is a high concentration of investors competing for the best deals, which produces a better market price on equity. Certainly, a too high valuation can also be harmful, since it risks a down round. With that said, over the course of multiple rounds, you need to maintain enough equity to fuel growth. If you sell too much, too early, it can stunt your future growth potential.

Outside of the Valley, one founder explained to me that it’s not uncommon to sell 50% of a company for a few hundred thousand dollars. If it’s a capital intensive business, it’s unlikely they'll have enough equity left to sell in order to make it into a big company. Investors, getting too much of a good thing, get a bad thing, which prevents their portfolio’s ability to grow.

4. Legal terms

It’s not uncommon to see companies move to the Bay Area and be stuck with crazy investment terms from a previous angel investor.

Let’s say an investor who’s invested $10k has the ability to veto an acquisition. Not only do custom terms cost a lot of money in extra legal costs, it can also scuttle a company’s ability to raise future rounds, since this small investor has an outsized impact on the future of the company.

Because of the sheer number of deals that happen in the Bay Areas, norms on what is reasonable and not reasonable have developed.

5. “Trust-based ecosystem”

Garry Tan explained to me once that Silicon Valley is a trust-based ecosystem.

Just like repeat interactions in the prisoners dilemma produce better behavior, so do repeat interactions in Bay Area. Founders and investors know that if they behave badly, they’ll get cut out of great deals in the future.

6. Community versus isolation

Ben Horowitz explains that the most difficult job as a founder is managing one's own psychology.

In Minnesota, no one understood what I was doing or why it was worth it. I constantly felt like a foreigner. I even remember demoing our product to a family member and the person just walked away. The day I moved out here, I demoed it for a friend - he was so enthusiastic about it that he then started introducing me to his friends. After working on the product for nine months in Minnesota, I never experienced that level of enthusiasm from anyone.

Starting a company is hard and doing it in isolation is even harder. In the Bay Area, you’re surrounded by a community of people who understand. That makes a huge difference when you’re building a company.

7. Business development and integrations (growth)

This is a huge source of growth for us.

The vast majority of the companies we work with are within driving distance. In the event there’s an opportunity, we can meet in person. I’m very confident that business development wouldn’t have been a source of growth from Minnesota. Here's a talk I gave last year at 500 Startups unSEXY conference about business development.

It’s hard to evaluate odds. Especially with outliers and a desire not to move. Groupon was based in the midwest (Chicago). Startups are generally binary. So, anything you can do to stack the odds in your favor, you should do. If it takes moving to the Bay Area to increase the chance that you’ll succeed, I would (and did) do that.

There are 33 more reasons to move, I just ran out of time. Vote for the panel and share your comments on SXSW Interactive's panel picker and I'll share more reasons to move! 

Photo credit

Setting your angel round up to fail

I emailed this to one of our investors in 2011. Fundraising felt like I was playing t-ball with pros. (photo from wikipedia)

I met up with a founder that was raising an angel round. He was actively raising, but was only having a few investor meetings a week.

I mentally ran the math (# of potential investors, amount they could invest, potential conversion rate and time allocated) and there was no way he was going to close the ~$1 million round he intended.

Indefinite raising is also a negative signal. Just like a house that stays on the market too long, deals get old and become increasingly less likely to close.

Here are some checks to make sure you don’t set up your angel round to fail:

1. Do the math

  • Number of investors you’re pitching
  • Range they'd invest (i.e., $25k - $50k, $100k - $200k)
  • How many people you could close - run several conversion scenarios

If you need a 100% close rate to fill 75% of your round, it won’t be enough. It’s highly unlikely you’ll be able to get a 100% close rate. Many investors passed on Dropbox and Airbnb.

Need to talk to more investors? I wrote a post awhile back that could help: 10 Places to Source Investor Meetings

2. Target a 1-2 month raise. No traction? Stop raising

You want to find out as fast as possible if your company is fundable or not. Consolidate all of your learnings into as short of a time period as possible, so if you’re not getting traction, you get back to work. Remember, it’s the work you do on your company that makes you more fundable - and permanently fundraising can prevent you from creating any value.

If it’s obvious you’re not getting traction, stop. It’s not only a waste of time and a company that raises indefinitely is a negative signal.

4. Have > 6 months runway when you raise

Make sure you have 6 months of runway left before you start fundraising. The number of founders I meet that don't know their runway is terrifying. (Don’t be the startup that accidentally runs out of money)

With > 6 months, you have a few months to raise, while also running a backup plan, which may be profitability or an acquisition. If you wait until you have 1 month left in the bank, you run a huge risk that your company will fold; if you do find investors, the terms will likely be bad because your BATNA is going under.

5. Set your minimum target carefully

Many founders give a range of how much they’d like to raise. For example, targeting $300 - $500k, $750k - $1m or some other target range.

What founders don’t realize is that some investors consider getting to the minimum as part of the investment deal. Investors may commit, but if you’re raising $300k and only get to $200k, they might not transfer the money. If you think about it, that logic sort of makes sense, since your company will need the capital to execute on the plan you pitched. They may want the money to be held in escrow or wait until for confirmation that the minimum amount has been transferred.  

Other investors won’t ask and will transfer the money immediately. For those that asked us, we sent a screenshot of our bank account to confirm that we hit our minimum.

6. Don't be sneaky

Sometimes I meet founders that try to game the fundraising process. One of our advisors explained that investors are pros at fundraising. They do this all the time. Founders rarely do fundraise. I always felt I was playing t-ball against pros - I sent that t-ball photo to one of our investors to show how it felt :).

It's unlikely that you'll out game or out maneuver anyone.  By trying, you may just end up burning bridges and scuttle a relationship that should be built on trust.

The solution is simple: don’t try to game anyone. Just be nice, honest and straightforward about what you're doing and try to find good partners.  (Treat investors well when fundraising)

7. The valley remembers

I heard Garry Tan say something that stuck with me - Silicon Valley is a trust based ecosystem. That’s great for people that are trustworthy, not good for people that aren’t. So, be the former.

If it seems like you’re setting your round up to fail, the good news is that you can fix those issues or just focus on building out your business. You can still build relationships with investors, but explain that you’re not fundraising - you’re just looking for advice (Meeting with Busy People). In the end, it’s a combination of good relationships and a good business that will help you get funded. [1]


[1] There’s always the pre- launch, post launch debate on fundraising. If you're a new founder, raising pre- launch is more difficult. You can pull it off, I just think it's harder. Just know when to stop raising if it’s not working (see #2 above).