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Valuing Advice

Giving good advice is hard, and it starts with asking the right questions.

Every day we’re given advice, solicited and unsolicited, from everywhere and everyone: friends, advisors, mentors, bosses, colleagues, thought leaders, over coffee, blog posts, podcasts, panels: literally everywhere. Advice can be good or bad: or consistent, unusual, cliche, unexpected, insightful, biased, valuable, worthless. Great advice can come from unexpected sources, and sometimes great sources can give bad advice.

The fact is, it’s hard to give good advice. It’s easy to talk, but hard to listen, ask the right questions, interpret what people say (and don’t say), and synthesize everything you hear and know to give the best advice for a particular person, at a particular time, for a particular issue. It’s not easy.

In my work I spend a lot of time helping entrepreneurs with fundraising, pitching, product and strategy. There are countless blog posts on the topic of what startups should do and how they should do it; countless opinions on how to write a pitch deck, how much money to raise, how to find investors, how to convince investors to invest, how to structure deals. The advice in the area is endless, but it’s also hard for an entrepreneur to understand and use, especially a new entrepreneur, because much of the advice is conflicting or confusing. It’s hard to grasp the nuance, individual biases, or specific market conditions wrapped up in everything one reads and hears.

If advice comes before a question, discount the value of it, instantly.

A lot of what I do starts with listening and asking questions: what advice are you hearing, what is the market telling you, what do you think? Does the advice resonate with you? Does someone’s suggestions fit how you want to pitch and position your business? What have you thought about but discarded, why did you reach this conclusion? And I’ll be honest about what I know and what I don’t know, being vigilant about being aware of my inherent biases or blindspots created by my experiences. Giving advice this way is far harder than simply telling someone what I think, but if I focus on listening and interpreting before talking, it’s far more valuable in the long term: for me and for the entrepreneur.

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A couple weeks ago I listened to 13 different pitches for 30 minutes each (a fun 6.5 hours), reviewing their pitch decks, hearing how each entrepreneur told their story, asking hard questions, and giving direct, actionable advice about how they could improve.

I love seeing how an entrepreneur tells the story of their business. I love hearing how someone talks about their progress, their thought process and their plans. I love reading a deck and thinking about the questions I should ask, the questions others will ask, the questions that someone is scared to answer. Much like a financial model, the artifact of a deck isn’t the most important thing: we can have different opinions on whether decks are unnecessary, critical, or somewhere in-between, but we can probably agree that coherently telling the story and strategy behind your business is mission critical for fundraising. And I think that a deck can be a vehicle, a teaching instrument, or an important element to helping structure and tell that story and be a valuable part of the fundraising process.

When I was raising money for a early-stage startup in 2000 it was a different environment with different expectations. We had to write detailed business plans, comprehensive financial models, as well as a detailed pitch deck. It’s different now: the audience is (mostly) more educated, there’s much more information being shared by practicioners on the web, so much more information and opinion and how to raise money, and the document expectations are far different: no more business plans, no more detailed decks, more of an opportunity to have a product to show someone, and thus more conversations about what you’re building and how it impacts people. There’s tons of advice today on how to create a good deck and how to pitch your business, but at the end of the day that “something” that separates great pitches from good is something that you won’t find in a blog post: it’s something about you and your unique story or position that allows you to convince someone that you’re going to succeed.

And that has to come from you. Listen to the advice, but at the end of the day, listen to yourself.

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