Originally Published: December 10, 2013
Advice for Startup Weekend teams
Startup Weekend is a gathering where entrepreneurs come together to share ideas, form teams, and build products over 54 hours.
My first and only Startup Weekend team, now known as Conferences.IO, is now a successful and fully bootstrapped audience response software company. We won the judge’s choice at our Startup Weekend in April 2011, and the runners-up from that event are also kicking ass. All-in-all, ’twas a great weekend, but the success of our cohort is unusual. Sustained effort from Startup Weekend teams is uncommon.
Since 2011, I have attended three more Startup Weekend events, as a coach. Coaches show up to work one-on-one with teams, providing feedback and advice. Coaching is a rewarding experience and I’d much rather coach than judge. Judges show up to listen to a five-minute pitch from each team, then award one as the company in which they’d be most likely to invest. Five minutes is not enough time to get to know a team. As a coach who works with teams for hours, I feel much more attuned to who really could be successful.
A lot of folks have asked how my team was able to keep going. I’ve given it some thought and aggregated advice from my experience as well as the experience of other successful entrepreneurs.
You need a leader
Selecting a formal leader is valuable for a few reasons, the biggest being that it’s the cornerstone of team roles. When people know and accept their role, they can execute. Typically, your ongoing leader will be the individual who led the team at Startup Weekend (which is usually the person who pitched the idea); but it doesn’t have to be.
Companies also need one specific person authorized to act in a leadership capacity, someone who can sign documents, organize meetings, and have the final say in major decisions.
Your interpretation of choosing a leader can be flexible. My team left Startup Weekend with three people, and we split decision-making authority by topic matter. As the chief technical officer, I made (and still make) technical decisions. Finance and marketing belongs to the CEO because that’s what he’s good at. Significant decisions always involve full-team discussion, but rather than vote like a democracy, the final say is deferred to leaders.
Have a goal
Early on, we had a meeting with a major player in our space. He asked about our vision for the company, and we struggled to answer. I will never forget the next thing he said: “If you aim at nothing, you’re going to hit nothing with surprising accuracy.”
Early stage, late stage, or post-exit IPO … you need to have a goal. Your vision aids in day-to-day decisions, since you can ask yourself how best to act today given your company’s direction.
Goals are not fixed — they can and should change as you learn about your market and grow. But you should always be aimed at something.
Trim the team
No large Startup Weekend team I’ve seen (5 or more contributors) has made it far beyond Startup Weekend. While extra hands can be helpful in the short-run, they eventually become a hindrance. Good luck getting everyone to every meeting, and good luck slicing the equity pie.
Convene your team shortly after Startup Weekend. Discuss your goals as a company, and determine who is serious about moving forward.
Here’s a trick: Set up a weekly one-hour team meeting (preferably in-person). If there are folks who cannot commit to even one meeting, they are not serious.
Last note on trimming: Verbal departure is not good enough. Get something in writing that departing members relinquish any equity/involvement in your venture. You may need to consult an attorney to assist in this effort. Speaking of attorneys …
Find an attorney. Find an accountant.
This lesson is for first-time founders. You may know a few things about the tax and legal ramifications of starting a business, but you don’t know enough, and you will not enjoy sifting through IRS documentation.
Save yourself a world of trouble by finding a business attorney and an accountant. Their services will be less expensive than you think and you will eventually pat yourself on the back.
Selling matters. (Dollars or users)
Now we’re getting into the serious stuff.
Sales are the lifeblood of any company. Inside Silicon Valley, sales are users. Outside of SV, sales are dollars. Whatever you use to measure success, make sure you’re going after it as early as possible, perhaps even before you’ve built an MVP.
I could write 10,000 words on the importance of sales, but I will just leave it as this: It’s really really really really really really important.
One framework for scaling growth: 10x it. Instead of framing the problem as moving from zero to 1,000,000 customers, frame it as moving from zero to 10. It should be pretty damn easy to get 10 customers, and if it’s hard then you know you need to adjust messaging or make a significant pivot. Once you have 10, move up a level and find the next 100. Then the next 1000. At each stage, your strategy will shift, and the lessons you learn at one level will help at the next.
Befriend mentors
It’s tough to make big decisions in a vacuum, so seek people who can be ongoing mentors.
Great mentors are folks who have some insight on your market and may have already built a business in that field. But anyone can be a mentor, even friends who are just starting out in entrepreneurship.
Keep your mentors updated but don’t overwhelm them with questions. Try to meet regularly for coffee or lunch. I meet with the teams I mentor roughly once every six weeks.
But … don’t rely on mentors to make decisions for you. It’s your company, not theirs. They don’t want that responsibility.
Learn how to manage time and tasks
You will quickly discover that your time is a scarce resource. Make sure you’re being productive by adopting a task management framework.
I personally use a variation of the GTD framework. My office wall has a whiteboard with every task (and subtask) I need to work on in the near future. Every morning I review these tasks, choose what’s top priority, and make sure I finish those items by the end of the day.
Be ready to learn
You’re not going to have every skillset necessary, so be prepared to learn how to do it on your own. For designers and developers this typically means learning about marketing and moving into full-stack development. For idea people and hustlers, this means learning how to create great content, how to do SEO, make screencast tutorials, and more.
Hustle sometimes
Startup culture puts hustle on a pedestal, and there’s a general belief that hustle is the determining factor in your business’s success. Hustle means you’re putting in incredibly long work days and work weeks (think 10+ hour days and 70+ hour weeks).
I think over-hustle is a sign of inefficiency. Any repetitive process that consumes your time is a terrific candidate for automation, or cheap outsourcing.
For example, if you’re devoting 2 hours a day to writing blog articles, you should:
- Review your blog strategy to make sure these articles are effective.
- Look at outsourcing the writing of blog articles to a well-trained third-party (cost will be $10-50 depending on length).
Don’t be desperate
Humans have an excellent nose for desperation. Just like in prospective relationship partners, desperation is a turn-off. No matter how badly your company needs something, never go into a meeting trying to win by way of pity. It won’t work. Portray confidence in your vision, your team, and yourself. Even if you desperately need a deal, act like you don’t. Customers and partners are attracted to companies that are confident.
Startup Weekend teams fall into the desperation trap because the founders are bootstrapping and inexperienced. They view every potential deal as a must-have, and they go into meetings willing to give away the farm if it makes the potential customer happy.
Success is lumpy
Unfortunately, success is not the product of a linear formula. You will not see outcomes that directly correlate with resource investment. That is, it may take a long time for your company to see its first big win. And then it may take a long time before your next big win.
That’s why building a business is a marathon, not a sprint. Patience and perseverance are essential traits of startup cofounders. Your company is not going to be an overnight success, so figure out how to build and sustain momentum so that your team remains motivated and hungry.
Follow other entrepreneurs
Don’t be scared! You are in the same waters as many an entrepreneur before you. Choose a few entrepreneurial role models, then follow their blogs and social media accounts.
I’ve found that reading what other entrepreneurs have to say is something that helps to keep me motivated.
Conclusion
Startup Weekend is a fun event. Not everyone who attends is serious about moving beyond the weekend. If you like your team and want to give it a real shot, hopefully this advice can be a primer to your post-weekend liftoff.
Thanks
Gratitude to Nathan Bashaw, Brett Kopf, and Paul Green for their feedback and contributions to this post.