With the spring holidays upon us, we decided to take a break from the usual tech distortion and hyperbole and since this is pitching season – and speaking of the holidays, next up is summer when investors kick back a bit to spend time with their families and/or take some vacation time, so we’re resurrecting an earlier column as a reminder, and we’ll get to why in a bit.

When you were a kid how many times did your parents say No! N-O, NO! More than once, we’d wager. How many times did they say, Yes, Y-E-S, YES!’ Bet I can count the number of times on one hand – zero. Never happened.

We did notice this at a fairly young age – long before we knew that there was such a word – that NO is an acronym. It was parent-code for ‘keep trying’ or ‘change the talking points,’ provided that you’d figured out the code. In some cases, we found that if we changed our approach or arguments, we could get a yes. Persistence pays. And the same can be said of investors. Investors hate to miss opportunities, so they don’t really like to say no. They like to hedge their bets and keep their options open. Sometimes they will give you a hard and fast No and mean it. Still, that said, things change, so one never knows if it truly is a hard no. Or they may suggest that they might be open to coming in next round, once you’ve proved your concept a bit. It’s that FOMO thing, in case they might have missed something the first time around, so they keep you warm and keep their options open.

No, by the way, is an acronym for Not Ordinarily:

Back in the day, Avner Ronan founded a company called Boxee, a cross-platform freeware media center with social networking features that eventually spun out the Boxee Box.  When he was going for funding, Avner targeted Fred Wilson of Union Square Ventures – a very successful NY based investor who saw billion dollar exits five years in a row – exclusively and did get the meeting with Fred, but Fred said No. Undeterred, Avner sent Fred monthly updates on Boxee’s pivots and progress, and stumbling blocks which they had overcome. The answer continued to come back as no. This went on for 18 months, until there came that one update that changed everything.

And Fred said ‘Yes!’

Or, Right! said Fred – couldn’t resist.

Confirming what we had suspected since childhood: that ‘no’ is an acronym. In some cases. You don’t want to pursue an investor to the point where he or she will take out a restraining order.

We host our Online Investor Insights twice monthly with a different investor and a small group of self-selecting entrepreneurs each time. Other investors also tend to show up as attendees, too, to hear what founders are working on,  FYI. It’s a great way for entrepreneurs to get to know the investors and directly ask questions without having to find a warm introduction. Networking events and conferences are another great way to do so, but we purposely keep the group of attendees small – and interactive – so that it’s more meaningful for both sides of the table.

We’re going to share some of the information that various investors have shared at these events and the pearls of wisdom that they have imparted. And speaking of NO as an acronym, in smaller groups, investors tend to say things they might not ordinarily say when addressing a larger group.

Howard Morgan, founder of Idealabs with Bill Gross, Founder of the New York Angels, founder of First Round Capital and Chairman of B Capital – Facebook co-founder Eduardo Saverin’s fund – offered the 6 P’s he looks for in a company: people, product, plans, profits, passion, and persistence. (Product also includes knowing the market you are going after, and planning mostly means financial planning.) Mr. Morgan also believes that one of the most frequent startup mistakes is coming up with the wrong pricing, whether it’s too high or too low.

When he said Persistence, he meant that every startup hits roadblocks. Investors want founders who are persistent and passionate about what they’re doing and who will prevail – who won’t let stumbling blocks stop them. Persistence, again, does not mean that he may need to take out a restraining order.

Some investors want you to be a subject matter expert, or to at least have one on your team. You hear that a lot. We mentor at top accelerators in NY and attend many accelerator demo days. At every demo day, without exception, each company will talk about how their backgrounds make them subject matter experts. Sometimes – usually – a startup is there because the founder experienced a pain point and decided to address it. Jeanne Sullivan, founder of Starvest and now at the Arcview Group, understands the pain point issue over subject matter expert – when a question came up – and said that she doesn’t put an inordinate amount of stock in that subject matter expert thing, or as she put it, “the Wright Brothers didn’t have a pilot’s license.”

Being a founder is a tough row to hoe, and there’s a high depression and suicide rate. Peter Shankman, angel investor and successful serial entrepreneur, remarked that, given this, it’s important to have honest, supportive people around you, rather than people who tend to constantly be overly critical. In fact, Peter advised that if you can’t change the people around you, then change the people around you.

One of our favorite pieces of advice came from Steven Messer, a very successful serial entrepreneur and angel investor who advised entrepreneurs not to go to investor, but rather, build a business and go the funding route only as a last resort. “Why would you want to go to an investor?” he said, “Frankly, you’d get better rates from the Mafia.” Neither we nor Messer are advocating that you do that.

Joshua Siegel of Acronym Ventures advised attendees to make sure to network with each other when attending events. You never know who’s in the room and how they can help you with your product, with building your team or whatever else you may need that you may not even know yet that you need. You never know what might come from it. Your next customer or strategic partner might be in the room.

Siegel also advised people to go to events and meet investors, even if they’re not yet looking for investment. It’s always good to establish a relationship early. In fact, the earlier, the better.

When Andrew Gluck of irrvrntVC spoke, one of the attendees mentioned that she had just finished her pitch deck. “No, you haven’t,” he said. He had mentioned that, while working with and advising one of his portfolio companies, and Gluck tends to be the first check in – together they had revised the deck over 100 times. “The deck isn’t finished until the round is closed,” he instructed.

Speaking of investor decks, here’s another point: once you’ve ‘finished’ your deck, read it over as if you’re an investor. Read through it as someone who can potentially invest money in your company, not purchase your product. A marketing or sales brochure is very different than a pitch deck. Is this the deck that’s going to move them to write a check? Well, no, but it better be one that intrigues them sufficiently to at least get you to the first meeting.

David Arcara of Laconia Ventures also advised the group to establish relationships with investors early. The day we hosted him, he was writing a check to a founder whom he had met some ten months before. And who had been following up with him as to his progress ever since. Said David, “You want to get to know your investors. I’m sure that you’ve heard that getting involved with an investor is like a marriage and that is not true. If that marriage goes bad, you can get a divorce. You cannot divorce your investor. That union is for the life of the company. You’re stuck.” Ok he might not have used the word ‘stuck’ exactly. But we’ll leave it at that.

Jake Crowley of Crowley-Capital also mention this when he spoke at a recent Investor Insights, so pay attention, founders.

Most investors like the founding team to have two co-founders. Why? Good to have a co-founder to bounce ideas off and get you through the tough times. Another reason: they like to know that – no matter which co-founder had the original idea – that person was able to convince another person to buy into it. While that seems to have changed a bit from what we’ve seen in some cases in this Age of AI, but who’s writing the check? How seasoned/successful is the investor or fund? And, as usual, time will tell.

As for why we’re resurrecting this column now, as we said, it’s pitch season and with the investors about to unplug a bit when summer hits, it’s good to get their feedback now so you know what to work on, have the upcoming off season to work on it and are ready for the next round once the next pitch season kicks in.

One of the reasons that David had taken 10 months to write the check to that solo founder is that the company had no co-founder. But he had gotten to know the founder quite well – the company had gotten considerable traction in those 10 months, the founder had been emailing David consistently with updates, despite the fact that he wasn’t getting a fast yes, and David was now impressed with what he was seeing and hearing.

“Did he manage to find a co-founder in that time?” we asked.

“No,” David answered.

“But you said you never invest in solo founders.

To which David answered.

“No, we don’t.” Then paused and added, “Welllll, not ordinarily.”

Have we proven our point? That would be Y-E-S. Onward and forward.