5 Learnings from Building and Exiting an Early Stage Startup
Actionable tips for early stage founders or aspiring entrepreneurs in a candid summary of an entrepreneurial journey.
5 Lessons in (less than) 5 Minutes
It’s been exactly a year since we exited Sherpa and got the chance to partner up with Micah and My Bag Check. My number one learning in our one-and-a-half-year journey of creating a luggage delivery service in London is the power of (and this is cheesy, but also key) the co-founder relationship. If you don’t wake up looking forward to spending the next almost 24 hours talking to and working alongside your co-founder, think twice about this partnership. Which, frankly, is more like a professional marriage.
I was excited to be asked to summarise my entrepreneurial journey by London & Partners for a mentor — startup mixer event. Turns out… it is pretty difficult to reduce our endless ups and downs into a simple five in five (5 lessons in 5 minutes). Here is my humble attempt at actionable advice for anyone building — or thinking about building — a startup.
Disclaimer: Views are my personal ones based on my experience with Sherpa, an early-stage luggage delivery startup in London. The focus of this short piece is on our day-to-day building and growth. Think of this as a few actionable ideas and learnings rather than advice. Every journey is different, so I hope you pick and choose what works for and resonates with you.
If you skipped the preamble — here are the five key learnings from my early stage startup journey:
1. Co-founder, co-founder, co-founder.
2. Be bold, be uncomfortable and just go for it.
3. Too many opinions are distracting — focus on the above.
4. Narrow down and focus — don’t try too many things at once (but keep an open mind).
5. Don’t doubt or underestimate yourself — nor waste time comparing yourself to others.
1. Co-founder, co-founder, co-founder. You hear this a lot. Seed stage investors base their decision almost solely on the team (once the idea, market, etc. stack up). However, from the co-founding team’s perspective, you need to think about the tough conversations and expectations upfront: How long are you willing to commit to this?; Where do you want to live?; How supportive is your partner of you spending all this time on a venture?; What are your motivations for building this company?; What are your leadership styles? ; How do you handle disagreement? The list goes on, but it is up to you and your founding team to face up-front and head on the issues that will be most critical for you both personally, and for your relationship with each other, as you go on this journey.
Action: Create a founder agreement. We thought this was a bit cringe initially, but it informed our future hiring as well as working relationship. Be sure you are comfortable discussing this together. Summarise the above questions in a two-page document that you sign at the bottom. Spend the day on this; it will feel great afterwards and you will keep referring to it at times when you least expect to.
Reading: Founder’s Dilemma. Thanks to the amazing MBA Pathways to Startup Success class that both my co-founder, Allie, and I took with Gary Dushnitsky at London Business School, we learned about many of the founder relationship struggles, downfalls and successes. The founding team still remains one of the top reasons for the success/failure of a startup.
2. Be bold, be uncomfortable, and just go for it. You will face hurdles every day (and sometimes every hour) during the early stages of growth. You are laser-focused on getting and proving traction. We very much embraced the ‘lean startup’ ideology and went on the market much earlier than we were comfortable with. At the start, we had a basic (and buggy!) website and started taking orders, often manually. Our very first referral code campaign was us coming up with promo codes (e.g. “xyqhw20” because it looked automated) and manually pasting them into emails. The more awkward you feel doing something, the more certain you can be that you are really being lean and hacky.
Action: Approach people cold and get their initial reaction to your idea. Instead of wracking your brain trying to get connected to the key decision makers to negotiate sales or partnerships. At the very least it’ll be great market research, at the most, you will find a customer. We felt weird about it, but at the very start, we would walk into hotels and ask to speak to the manager about improving their guest experience. It didn’t come naturally… and we got a lot of “no’s”. But also a few key “yes’s”.
We also did guerrilla marketing, handing out flyers on the tube walking through carriages and in train stations, and even delivering the initial hundred or so bags ourselves (via the tube as we didn’t even have a car yet!).
3. Too many opinions are distracting — focus on the above. Don’t spend too much time on pitches, applications, conversations. This is not to say funding is not important and that you should bankroll yourself and forget about financing. Instead, being smart with your time and efficient in your efforts is so important and something we were not so great at. The most precious resource you have as a founder is your own time.
Action: Split up work between the founding team; target your investors/create a funding strategy. You don’t all have to do everything and attend each meeting together. We could have managed our time much better; dividing and conquering. You also don’t need to be building a VC-backable business from day one just because that’s what’s all over your news or social media. Explore all options available to grow your business (catered to the nature of your industry). Even though every conversation was helpful in its own right, we should have been more targeted about who we spoke to and when. Be specific about what you want to achieve with every meeting and conversation. Be efficient with your time by being strict about when you engage and with whom. In hindsight, we spent a lot of time talking with investors (many of whom didn’t have any knowledge of our sector) and getting too many opinions just made us indecisive.
4. Focus — don’t try too many things at once (but keep an open mind). Again, be careful of too many different opinions. Because they were so heterogeneous, and we put so much value on them, we often found ourselves brainstorming and pivoting to satisfy everyone.
Action: Focus on what feels right for you. Go with your gut. Unless you are a capital-intensive infrastructure business, you will be able to move fast and pivot when you realise a solution is not working. Don’t overthink every single action. It is very important to choose an anchor target customer set or partner. Once you succeed at it (or don’t), you can move on and try your next set of ideas. Many entrepreneurs want to move faster than is physically possible and try to find solutions for their whole market immediately. That is why many startup decks and websites can be confusing; the value prop is not clear. Cut out the noise, double down. Too many different things at once will distract you (e.g. trying to make your website work for both a business customer and consumer customer, assuming you have limited resources).
With all the advice and opinions you get, you can try splitting this up into different categories and prioritise those within the impact/effort matrix e.g. by customer segment, investor, competitor, partnerships etc.
5. Don’t doubt or underestimate yourself — nor waste time comparing yourself to others. Just a few words of cheer for all the entrepreneurs being brave yet at times unsure. You are not alone.
Our Sherpa exit was early, so we kept thinking we’re not big enough, we haven’t proven enough. But we should be proud of what we achieved in a short space of time. It is too easy to get sucked into a scrolling loop on social media; seeing other’s successes and feeling like yours are not adequate. PR is a powerful machine and unicorns are constantly taunted as the definition of success. Easier said than done… but be proud of the small wins and know that every other entrepreneur has felt the same way as you — uncomfortable. There is a lot of ambiguity in a startup and that is when you are learning and growing. If you felt comfortable all the time, you might question the speed and direction your business is going.
At Sherpa, we tried to celebrate every positive conversation that pushed us ahead a bit more (often followed with some disappointment — and that is completely normal).
Action: Write down everything you did and achieved. The frequency or time period is up to you — this helped Allie and I during our exit negotiations. It will also help consolidate your thoughts and boost your confidence, to see everything you managed to build in one place.
