Founders, Let me start by saying, with local elections, a tiny number of votes can swing an election . So, your vote truly matters. A few companies just showing up can swing an election and dramatically impact policy for years to come. We’re in the middle of a housing crisis. People are paying an exorbitant amount for rent. Teachers and other workers can’t afford to live here. Homelessness is…
Ten person startups (or smaller) often have a lot of generalists. Everyone does a little of everything, which is what can make startups exciting. We had “support / office admin,” “product / support” positions and other combinations. The reason startups do that is because they don’t have enough admin or product work to warrant a full-time role. When you grow past 10 people to 15 or 20, that…
I’ve received a lot of feedback about startup ideas over the years. I had this ‘aha!’ moment, when I realized I was in a Catch 22 and if I kept listening to people, I would never start a company. It seems like there are two reasons people don't think a startup will succeed: It has been ‘done before’ It hasn’t been ‘done before’ and if it were worth doing, someone would have done it. It's a Catch…
Originally posted on the HelloSign blog . The image above sums up how I think of everything at HelloSign . If you want a snapshot of what’s going on in my head, it’s an image of a circle with three different pieces: customers, revenue, and team. This is how we will build a significant company. We rolled this idea out about a year ago. I realized as we grew from 10-20 and 20-30, not everyone was on…
My friend had a major site issue and she was up all night fixing it. Fortunately, by the morning, everything was fixed and none of her users noticed. Good times. She asked if I have any tips on managing the ups and downs of a startup? Ah, the things I’ve seen! I’ve had a lot of time to think about stress. Founders can be comically optimistic when you ask them how things are going. No matter how…
I met up with a friend a while back who was running a super lean startup team. It was a team of around 10-15 people, working long days, six days a week. He shared some insight into a few problems he was facing at the time due to the team being overwhelmed. I can see the appeal of running at capacity, since staying efficient is key. In the early days at HelloSign we ran really lean, but we were…
In 2008 a startup called Modista created a great new way to display goods on eCommerce sites. Investors were excited. In 2009, the founders decided to raise and had $600k in commitments from investors. Before the founders collected the money, Like.com sued them for alleged patent infringement. Patent litigation can cost $1-$2 million. Their investors decided against transferring the money and the…
Before we launched HelloSign , I remember showing HelloFax to a family member. This person was normally supportive, but he took a glance and walked away. He wasn't the only one. A lot of people wouldn't even look. I was the only believer. Belief is the most important component for a startup. Most companies are born and die with one believer. Maybe they had zero believers, since even the founders…
There’s always talk that we’re in a tech bubble . I heard about it when we raised our first round. Then, heard it again when we raised our second round. It’s never easy to know if we’re in a bubble — if we were, all of those people writing about it should be shorting tech stocks. The bubble writers would be the richest people in the industry. I’d love to read an article like this: 1) We’re in a…
Guest post. Originally posted on The Next Web . ---- When we went out and raised the first time (four years ago), we hit our fundraising goal. We had additional investor interest and almost closed the round. Instead, our advisor pushed us to keep going and we raised two times that amount. The second time we raised, we took on three times our target. It took our advisor serious effort to convince…
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…
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…
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…
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…
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…
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,…
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…
It’s a big year for HelloSign . We’ve grown from 11 people to 26 people so far this year and we’re looking to double again in the next year. Here's more on what we've been doing to scale: http://blog.hellosign.com/leveling-up-hellosign/
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…
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…
People often advise raising more than you think you need. Years ago, we raised double what we intended and it had a hugely positive impact on the company. ( Investors and advisors: the crowd, the ringside, and your corner ) Yet, I’m starting to see a downside of too much capital: new founders with years of runway and no external pressure to perform. Imagine a team that: Raises a lot of money (3+…
Stephen Levy recently wrote about a team of YC alumni, Google and others to help fix HealthCare.gov. They've made a huge impact. Dan Portillo , from Greylock, is now helping put together a tech team to help the Veteran Administration (VA). My brother is a veteran and he ran into a lot of issues at the VA. It was so frustrating, he ended up buying private insurance instead. If anyone is buying…
“I refuse to join a club that would have me for a member” - Groucho Marx We were interviewing for a role and had already talked to 30+ candidates. If we talk to 30 people, you can imagine how many resumes we looked through and phone screens we did to get there. We finally found someone who was a great fit. Instead of going through the entire process, like we normally do, we skipped one of the…
HelloSign had a big spike in support needs awhile back. The growth was great, but at the time, we didn’t have enough support people to meet that growth. Since we’re committed to closing out every ticket each day, the support team worked long hours to meet demand. [1] People often advise only hiring when you absolutely need to hire . There’s some wisdom here - it helps prevent a bloated team and…
I remember showing HelloSign to a family member. He barely took a look before getting distracted and walking away. Of all people, you’d imagine that family would be the easiest sell. Yet, working on a company comes with a lot of rejection, whether it’s apathy, passing on an investment, or a user not signing up ( The rejection book ). I see a lot of founders resent these people. I’ve grown to think…
I remember hearing about a company with an extremely charismatic CEO. The company wasn't doing well, but he was a compelling individual. He'd give a talk and the team couldn't help but believe in the vision. Investors believed too. Everyone got a jolt of energy. But, as soon as everyone got back in the trenches, people realized that none of the things the CEO said mattered. The company wasn't…
A few years ago, I met a founder with only two months of runway left. In two months, his company would shut down because he didn’t have any cash to support it. He wanted to discuss whether he should start fundraising for his second round. That’s some scary shit. We should have had that talk when he had 6 months of runway left. Here are the two scenarios you should never run into: You don’t know…
I remember meeting up with a new founder who was stressed about the fundraising process. Fundraising can certainly feel stressful, but I realized that most of the issues could have been solved by asking the right questions. When you’re less confused about the process, it makes the process more predictable. Here are some questions I found helpful to ask when meeting investors: 1. What kind of…
I hear about investors or advisers as either 'helpful' or 'unhelpful'. I think that misses the nuance of the kind of people you need involved. To get the support you need, it’s important to be deliberate about how you pull together this key group of people; the right individuals can have a significant impact on your outcome of your company. Here are the categories, as I see them: 1. There's the…
A few years ago, I remember talking to someone on the team and saying that we had to grow faster; the status quo wasn’t working. He mentioned that to another person on the team. When I ran into that second person on the bus, he was really stressed. I inadvertently created stress about a problem, but didn't communicate a solution. Everyone could feel it, even though I only talked to one person. In…