How to give advice to Founders

One of the benefits of being a second-time founder is experience. You process and react to things differently. Something that has really hit me as we’ve ventured down this journey is how differently I process people’s feedback this time. The first time round my response was more emotional and existential. It took me much longer to process negative advice and it drained me. This time I register the information I need and move on. As Alban Ivanov says about opinions, “I’m not arrogant, I just know I’m the best”. That sums up Founders well. 

I will borrow a framework that I’ve heard used by military veterans and professional athletes- they refer to people not in the profession as civilians. It is used to refer to people with strong opinions who have never served/played. Calling someone a bad defender because Kevin Durant scored 50 on them is a civi take (because it is incredibly hard to stop KD).

Entrepreneurs are trying to disrupt something, so you need input from civilian “experts” as you explore your idea. The problem is that most civilians don’t have a clue how to provide you the insight and advice you need. This post is meant to help civilians provide advice to entrepreneurs in the most constructive manner.

Let’s start by addressing the primary divide between entrepreneurs and civilians: world view. An entrepreneur sees a problem and is motivated to solve it. Civilians see a problem and, at best, wish someone else would fix it.

For example, we spoke with a senior exec knowledgeable about social media marketing and this person talked about the challenges that consumer brands face with increasing acquisition costs. It was hard to not walk away wondering if it was even worth trying. Now, acquisition cost is a real challenge, but if you are dealing with it, then you are likely doing plenty of other things right. Conversely, in another conversation with a Founder, he mentioned the same problem and immediately mentioned Traction as a great resource to think about testing and iterating acquisition channels so that you don’t find yourself over reliant on expensive channels. That second conversation was way more valuable to thinking about how to approach user acquisition than the first.

So, here are a few recommendations for non-Founders who are asked to provide feedback:

Be positive

Let me be clear- I am not saying blow smoke or lie. We need to hear the unvarnished truth. However, we don’t need to be told all the reasons why it won’t work. This entrepreneurial journey is hard enough, so see this as your opportunity to make the journey a little easier for us. You want to frame perceived challenges as “you will want to be prepared for” or “the general opinion in the market is ____, so you’ll need to prove ____ to convince them”.

For example, if an American asks me about entering the European market I need to make sure I get across to them that the European sales cycle and experience is different. It is unlikely that your business will grow as quickly early on in Europe as it did in the US. That doesn’t mean you shouldn’t enter the market. It just means that you need to be aware of the nuances and how to account for this reality in your plan. So, rather than saying “Europe’s a (enter negative phrase)”, I’d simply highlight the 3–4 key drivers and then offer some examples of how I’ve seen it work or not. The person can then incorporate this into their planning.

Ask questions

Ideally, the entrepreneur has given you a sense of where he/she is in their research. However, it is hard for a lot of people to admit they might not know much. This is much easier the second time or if you are someone with high self-confidence. I recommend being overt about why you’re asking- because you want to help, and you want to know where to start to maximise the benefit. Good questions to ask:

· Where are you in the process?

· What do you know about YYZ topic so far?

· What specific topics are most interesting to you (and why)?

Provide context and details

As someone with experience in the market you have invaluable information for the entrepreneur. Providing the context of your specific experiences (we were an established player, or we were the non-German supplier) is a great starting point. From there, it is great to talk about the successes, failures, and lessons learned from the experience.

Provide Encouragement

This one is the superpower. If you think the entrepreneur is on to a great idea, then tell them. There is nothing better than an expert telling you that you are on to something.

However, you don’t have to be a kool-aid drinker to provide encouragement. I think of encouragement as what American football coaches used to call “forward positive momentum” — Success as a Founder is being in perpetual motion. If you are sceptical, then recommend that the person go speak to three potential prospects. Even better if you can connect them to one. This will help them keep moving forward.

For example, when I started Hillgate I thought for sure our target market would be SMEs. Someone recommended having a few conversations to see the response. It became clear that SME’s budgets and perception of “consultants” was going to make this very hard. We pivoted to Enterprise and found our path.

The feedback wasn’t a commentary on the viability of the business, but rather about the best route to market.

One of the best parts about starting a new business is seeing all the people who are willing to help. My hope is that this post helps people match their positive intent with advice that makes it easier for (potential) Founders to keep moving.

Too many people get discouraged by early feedback from experts that makes it seem like an impossible task. It is hard. It is not impossible.



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