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Founder Newsletter

Biggest Learnings from Wefunder Workaway

on Jul 3 2019
Studied in 3 countries & at the United Nations. Kiva alum. Started a plant-based meat company. Soccer player, hiker, and craft beer nerd.

This June, we took 16 founders and 8 mentors to Hawaii on Wefunder Workaway, a trip designed to foster connection between idea-stage founders and propel them forward along their founder journeys.

The trip was structured similarly to early-YC. Each day, we worked (or, some hiked and snorkeled). Each night, we reconvened for an intimate evening workshop followed by a group meal and fireside chat led by one the mentors (plus one special guest, Nick’s grandma).

The focus was largely on sparking momentum in a startup — whether it be tech or CPG, but many of the learnings are relevant for founders at all stages...

Night 1: Legal

Shruti Shah from MoveLoot led the legal session*, mostly focused on incorporation for our idea-stage founder audience. We learned about C Corps vs. LLCs, common stock and preferred stock, and that lawyers are our friends. 

Some tips & tricks she shared:

  • File 83b (and this license plate to remind you). Hopefully all of you know this by now, but filing your 83b election form when you incorporate and purchase shares ensures that you aren’t paying taxes on the future value of this stock (because as you might imagine, this gets expensive)
  • Do the work in advance yourself to save on legal costs. Get template from law firm, fill in the blanks yourself, then have a short call to ask questions
  • Be a squeaky wheel, otherwise your work can get de-prioritized
  • Don’t get sued (obviously). Specifically with regard to people who do projects for you. Always pay them and have a contract for their work, otherwise you can get sued for back pay.

(*note: Shruti is not a lawyer, neither am I)

Night 2: Make Something

Founder & CEO of Wefunder, Nick Tommarello led the “Make Something” session (again, designed for early-stage founders). But if you’re launching a new product/feature, are pivoting the business entirely, or are stuck on something, keep reading.

The formula for starting out…

The don’ts...

  • Don’t do endless user research without iterating on a product and getting data in action. People lie. They want to be nice. Only their actions matter.
  • Never spend more than 6 weeks on an MVP. Start with a simple landing page and a call to action. Do people take that action? Focus, then focus again. Keep designing to get 10 people to really love you.
  • Don’t blindly listen to product feedback from non-users. Again, only actions matter.
  • Don’t focus on an abstract vision. Focus on an immediate problem that a user has now. If Nick’s grandma doesn’t understand, you’re on the wrong track (we actually tested this because Nick’s grandma was there)

The dos…

  • Be ok with doing a lot of bad work (perfection is slow and you’ll probably be wrong at first anyway)
  • Default to action. Don’t over-think, over-plan, over-debate. Just do it, get data, iterate.
  • Decide fast (speed > being right). It’s better to make a lot of mistakes and learn from real-world results
  • Design for 10, not 10,000. The sooner you make mistakes and iterate, the better.

Most importantly: Believe in yourself!

Night 3: Product

The product workshop was led by Daniel Ha, founder of Disqus. He walked us through 4 good habits to adopt that will help drive good product decisions…


  1. 1) Start with the customer. Figure out a way to figure out what your customer actually needs, not what you think they need. Or what’s cool. Keep it to one type of customer at first. Establish the job that needs to be done and work backward from there.
  2. 2) Start small & keep improving. Starting with an MVP forces you to learn in a structured way that you can iterate faster. Each step should get you closer to figuring out your market by delivering value to your customer.

  1. 3) Be thoughtfully basic. Instead of considering everything that could be possible, go deep into the fundamental problem that you’re trying to solve. Avoid added complexity and deliver strong on the basics. Start with high impact + unexpected features, followed by high impact but expected (“you should already have these”) features. “Neat” features help with stickiness but should be developed after the higher impact ones.


  1. 4) Use data correctly. In the early stages, let data inform your path, not drive it.

Night 4: Fundraising

We talked fundraising with Spoonrocket founder, Steven Hsiao. His advice was “Go raise on Wefunder.”

Just kidding. 

vs.

Ouch. (See, he should’ve stopped after “Go raise on Wefunder” 😉)

Steven’s (real) pointers…

For female founders, raising capital from VCs can be much harder, which is why more female founders are tapping female VCs and angels. Shruti’s advice was to talk to friends who’ve had good experiences with their investors. There are also lists floating around the interwebs for which investors that female founders should avoid.

Joining a community like Female Founder Community on Facebook or Elpha can be a good way to learn about different investors as well!

For tech-focused founders, you may also want to check out Lunch Club to meet investors in your city.

Night 5: Culture

Chris Smoak, co-founder Atrium gave us the low-down on culture, which can be made or broken from the early days in a startup.

“A company’s culture is your team, their shared values, and how those are exhibited as actions when you work together” - CS

Goals of a healthy culture:

  • Alignment & focus
  • Happy, more productive teams
  • Ability to recognize problems and address them
  • Public image; hiring & customers

To build a healthy culture, start early! Here’s how…

  • Formalize company values. Include everyone and pick 3-6 company values that you’ll promote within the company, use to evaluate employees and candidates, and acknowledge employees who exhibit these values.
  • Set a vision. Then write it down, along with your plan to get there. Why? Your vision shows up everywhere: recited by employees, when hiring, with friends, with customers, etc.
  • Encourage employees to organize. Promote employee ownership through working groups, hiring practices and diversity, and set up a structure where these initiatives can be presented to ownership.
  • Formalize ways to communicate with your team. This is where the values and vision are repeated, over & over, consistently. Think things like weekly all-hands, posters, stickers, swag, and your website.

To keep your culture on track, pay attention! Look for warning signs like office politics, lack of engagement, low quality meetings, and lack of diversity. Take action by providing office hours for employees to talk with the founders and/or leadership, solicit broader feedback through surveys, implement OKRs, and get HR involved.

Night 6: Luau!

Overall, the biggest value-add for participants of Workaway was being surrounded by a kick-ass crew of people who are also building a startup, or who know what it’s like to build a startup from first hand experience. This was reflected in our celebratory luau as the best part of the trip: the people.

Blurry, but the only group shot

It’s super important to be surrounded by people who will challenge and inspire you when building a company, along with having a group of people who will ground and support you through the ups and downs. We (unfortunately) can’t jet off on a Workaway every time we’re stuck in the trenches, but we can tap into the Wefunder alumni community, which is an incredibly rich network that can be a source of support, inspiration, and knowledge for when you’re launching your next product, funding round, or growing your team, etc.

In the spirit of Workaway, we’re hoping to foster more connection between Wefunder alumni founders via office hour calls. Want to sign up to connect with another industry-relevant founder? Let us know here.

Want to be notified when we host our next Workaway? Sign up here.

Thanks for reading!

Product session led by Daniel
Special appearance by Nick's Grandma

The house where we convened each night
Being Moana
Contemplating the night's session
Taking moments to reflect at Wiliwilinui peak
New friends!