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Serial Entrepreneur – EP57: Crafting a Winning Pitch


It’s all about perfecting the pitch. That’s what we’re going to be talking about today. Our special guest Lil Roberts is coming on in a few minutes. And on this show, we try to break the code. We try to figure out what it is that these serial entrepreneurs do over and over again. What is it? Lil Roberts does over and over again to succeed at many of her companies. And, that’s the challenge.

That’s the question. These serial entrepreneurs can start scale exit and repeat that over and over again. And we really want to figure that out. So we’ve recorded about 55 episodes and you’re now you can listen to those episodes on your favorite podcast channel. If you go to Spotify or Apple or Amazon and you type in serial entrepreneur club, you can listen to all of these episodes.

I’m telling you this. If you listen to them, you’ll get an MBA in entrepreneurship. There was so many great speakers we’ve had on from [00:01:00] Jeffrey Moore to Bob . Who was, you started to unicorns. It’s just incredible. The people we’ve had on and today again, we have Lil Roberts and she runs a company called

It’s an AI accounting software company. And in full disclosure, I invested in her. I just signed another document. So a second investment she’s proven the pitch to me. She definitely has the goods when it comes to it. And she’s also won a number of pitch competitions early on in her business.

But Lil, why don’t you just kick it off, just tell us a little bit about your business yourself and just your pitch journey, but what I am also hoping for in the audience, and you want to ask Lilit question, please raise your hands. Give us a little background here. Hold on. If you’re in the audience and you also, I’m hoping we can do this in the last half hour and you want to come up and pitch your business for 60 seconds will give us the 30 seconds.

We’ll get 32nd or 62nd pitch and we’ll, hopefully you can get some [00:02:00] some tips and tricks from Jeff here, myself and Lil and Michelle. Just a little bit about your backgrounds and your pitcher. Thank you Colin. And thank you also for joining our round that we’re currently closing and hello to everybody out there today.

It’s great to be on with you and and Michelle and Jeff and everyone. Journey, much like yours, Collin, right? Serial entrepreneur or multi-business entrepreneur. And all my businesses have been different industries. And, as people that are listening on, which I think are probably a lot of entrepreneurs that are in clubhouse today, we just all like to solve problems, right?

So we see the world through the eyes of how do we solve a problem build a great business with a great team and and help people. And so that’s what we’re doing at Zendesk. We do online bookkeeping and accounting. We give self-made entrepreneurs, financial visibility to their financials and peace of mind and give them their time back.

But today we’re going to have a lot of fun. Cause I love the pitch. And I love the art of the pitch [00:03:00] and how to pitch, and I love helping entrepreneurs crafting their pitch decks. Yeah. And I remember just that, I think it was the day or two days before the pitch competition here in Miami at emerge.

And you came to my house and you sat in their little home theater. We have there. And we put it up on the screen and myself and you also Martin from boxy charm were in the room and we were giving you some advice and some tips and tricks and whatnot on how to make the pitch.

When you first started out, what did you learn? Like we know with those first couple pitches, what were some key takeaways that you learned. And thank you. And yes, when I was at your house that night, I’m like rip me apart guys, and you guys did. So that was great. It, and you have to be able to, that’s the way that you’re going to get the best pitch is you got to ask people to continuously rip you apart so you can refine it.

So what I’ve learned, and as I was, out at Jason, Calacanis his program for 16 weeks after we won emerge, we had the opportunity to go out [00:04:00] and it’s about, your pitch has to be short and concise. There’s an old saying, right? That, if you’re going to talk for an hour, you can write that pretty quickly.

But if you’re going to talk for three minutes, it’ll take you a lot longer to prepare for that because you have to carefully choose your words. And so when it comes to a pitch, it’s the same way. It’s, be short, be succinct and be to the point make sure that people can understand clearly.

And I believe that you have somebody until you lose them. So what do I mean by that? That when you are doing your pitch, you have their attention. The minute you lose their attention, you’re never going to get it back in your pitch. I like to come out swinging, so I like to come out and, metaphorically punch somebody in the face, to where you’re like, you’re catching their attention right away. And then you have to move quickly because if you see them glance at their phone, they’re gone and you’re not getting them back

now. What are some of the key components that you need in your chicken? Chicago? Obviously, I think one [00:05:00] of the things to kick it off would be, what problem are you solving? And if you can state that right out of the gate, I think that sometimes can get the potential buyers to say, aha, that’s interesting.

So is that, so what are some of the key components in. If you like Collin, I, I prepared as I always love to be prepared. So I prepared. What, so when you’re doing a pitch deck, typically, you want to, a great pitch is a pitch that you can do in three minutes or less one thought per slide, you want 12 to 15 slides.

And what you want to do is you want to come out your front slide, which is a slide that’s going to be up while you’re waiting to get started. That slide needs to evoke an emotion. No matter what you’re doing, there is an emotion to your business. And so that slide needs to evoke an emotion and it needs to have hardly any words I tell people, try to keep your words that describe your business to five to seven.

So that’s where you have to like craft and craft. Then as you [00:06:00] go into your pitch deck, then you want to do problem solution. If you have a demo, take a slide or two that shows. Then you want to have your, after your demo, what’s your total addressable market. What is the competition?

What is the business model? Business model is what is the financial business model? How do you make money? What is it be sure that they understand that then your team, the traction that you have traction and revenue. So they always want to see investors want to see up into the right customers like, where if you’re global or if you’re concentrated or what type of customer have something that shows that, and then what’s your ask and you want that to be 12 to 15, less than three minutes.

I have a question for you. You mentioned if you have a demo, keep it to one or two slides, but what are your thoughts on if your product, if you have a prototype or if you have something that’s functional, what are your thoughts on incorporating an [00:07:00] actual demo, as opposed to just screenshots.

You need to be able to so really a great question, Jeff. So you, what you want to do is you want to have your demo running in the background for 10 seconds. So that slide can be that, that you have an animation of it running. Don’t bring up your actual demo. You’re opening yourself up for bad internet for slow response and you can’t control it.

So if you already have a 10, second, 10 to 12, second video of it running, all you want to show is that you have working. They don’t, take what your pitch deck is designed for is for the next conversation. When you’re standing up in front of group of people and you’re pitching and you have a three minute pitch, you need to stand out the clearer that you are in a more succinct than I can get into all the things about if you guys want to about, how to stand, what you should, we’ll go into some of that.

Cause I think it’s important for people because it’s more than what your deck is and what your pitches. So with that, if [00:08:00] don’t fiddle around and you’re going to lose your time, and then you’re going to lose the audience, have it running in the background for 10 seconds. The other piece is I see, Collin and I both are our mentors for the Nova innovation center, which has an incredible innovation center.

And so we mentioned that incubate 98 classes and. On pitch decks. Don’t have a lot of words. It’s gotta be one thought per slide and you need to do it with an image, a picture. And then maybe a couple of words, but don’t have a lot of words. That’s a standing three minute pitch deck. If you have a longer talk through deck those can have more words and those should tell the story by the tops of the sentence that’s at the top of every slide is how those work.

You think it would be helpful to run into, how your stance should be. And some of that stuff, you guys think that we love that stuff. That’s great. Okay. Perfect. Just speak before you get to that one more thing. Cause you mentioned about the slides and the technical issues with doing a [00:09:00] demo, but I actually witnessed this happen to you once on stage.

So I know you were prepared for it, but you need to be ready for your slides to not work even right. So it’s really important to, yes, you want to have those slides and you want to have the big images, draw the emotions one or two words, but you also need to be prepared to give an awesome pitch without your slides, should somehow the power go off for them.

Would you agree? A hundred percent. So to clarify that, and the reason why I’m laughing. So at emerge Americas 2018, we made it to the first slide that to get it, to get to the to the main stage. The first stage gate was to be one of, out of 102 hundred and 10 companies to be one to 25 companies doing a three-minute pitch on stage that’s timed.

And then they turn you off. Why was the very first company going on? And when I went on the clicker, didn’t click because they didn’t have a [00:10:00] rehearsal to make sure that clicker was going to work with your deck. And so I went up and the clicker didn’t work. And so I continued on and then once they got it working, I caught the slides up and didn’t miss a beat.

Jeff, and and so that’s where it didn’t work, but if I would have gone, oh, geez. A few seconds for them to get it working. I wouldn’t want to get those 20 seconds or 30 seconds back and I didn’t get them back. They, that clock still went off at three minutes and that was it.

The other thing is if you go over the investors that you’re pitching will think that you’re not prepared and that you didn’t do the work and that then flows into what they think, how you’re going to run your company and how you’re going to execute. So it’s very important. Let’s go with and the way that I was able to do that is that when I prepare for a pitch and I craft a pitch in order to craft a pitch first, know who your audience is, and then use post-it notes.

So write what you need to do the big thoughts of the slides that [00:11:00] you need to do and put them on post-it notes. And then that way you can start to put them in order and you can move the order around. And then it’s like with anything, you’re going to go through revision after revision, but before you give it to somebody to ask.

Prepare the deck for you, try to get your thoughts as organized as you can, then you give it to, you give it to a incredible, like we’re very fortunate. Our designers is, best in class. Unbelievable. Our decks are always gorgeous and people comment about our decks. So then make sure that you find a designer that you resonate well with, that can put together.

And then practice with your deck. And when you’re first learning your deck, don’t worry about your timing, just practice, and then you’ll refine your deck some more. And then when you get past that, then type up what your pitches and when you actually see it on paper, type it up and print it out like the old school, and then cut through the unnecessary words.

If you say the, and you don’t need to say the cut, the, if you [00:12:00] say of O F cut that, cut all the words you can cut, then practice with a clock to see. And if your pitch is three minutes, you want to end it at two minutes, 45 seconds. Because when you get to the stage and you’re pitching, you’re going to go over.

You may stumble on a word, something may happen. So give yourself a few extra set seconds for that. And then go to office Depot or order online. One of those clickers that, that you normally get when you go up on stage to actually do your pitch. By one of those, because after you figured out your pitch and you’re doing it sitting down now, you got to get to the final stage and that is, have it to where you’re standing across the room and you’re actually using the clicker.

And what you don’t want to do is you don’t want to, have your hand motion. Every time you click, like you’re throwing your arm out, you don’t want to do that. You want to figure out how to keep your arm that has the clicker down by your side and click it when it’s down by your side. If you use your hands to talk, [00:13:00] be very conscious of how your hands are never point with a finger, have your hands open.

And then your physical stance your physical stance is that you want to stand in a confident stance and a confident stance is shoulder with a part, have your legs shoulder with. Upright, make sure that you’re not rounding your shoulders that you’re in an upright position.

And I always recommend, and I do this myself, but people that I coach on pitching, I always recommend that you do the Anne Cuddy, C U D Y D as in door, C U D Y, and Cuddy power pose. And what that is that you, you put your hands on your hips and your two minutes silence and you breathe in and out, your eyes are closed.

So set your electronic set your timer to go off in two minutes, breathe in and out and think of something really incredible that makes you happy, whether it is, a Sandy beach or a Palm tree or snow or whatever it is. And that’s been [00:14:00] proven for people when they go on interviews and things like that.

If they do the power posts that they do better, that you’re more comfortable in your body. And that’s what pitching is. It’s a. Being able to deliver a story in a way that people understand that succinct and that’s empowering and inspiring, and that you yourself are very comfortable as you do it.

I’ll pause. Yeah. It’s interesting about the pointing the fingers. So when I was doing a road show for our IPO in the two thousands, mid two thousands I was, one of the first meetings I had, I was in the meeting and I was pointing my finger at the potential investor. And afterwards it was RBC was our underwriter.

And they, you obviously gave me advice and said, don’t do that. Don’t point your finger. And yeah, there was just, it was a very interesting, the other feedback I got was when I was in larger groups and doing speeches, they actually wanted me to calm down a little more. I was a little too enthusiastic.

[00:15:00] Is there a balanced, because when you’re an investor, you want to see. Entrepreneur is enthusiastic and excited about the business, but they don’t want them to go too far. Is there a balanced, like in between Lil that have you had any issues with that yourself or is that, was it just me? I get to sometimes you get very animated and excited to call on which I love.

Yeah. I think what they’re looking for is they’re looking for you to be to the point and to be confident and to know your numbers and I think it is important. So I think that you can’t be overzealous about something, they want to feel the confidence, they want to feel that you’re comfortable in your skin.

And that you’re confident. I think to me, I think that stands out. They have to like your energy like they have to like your energy. Yeah. And the other thing I learned in that. Process. We did a, I think we did 37 meetings in two weeks and about seven or eight different [00:16:00] cities in north America.

And and we was a successful IPO, we did close it. So we were able to raise the money, et cetera. But the other thing was that there were so different each meeting, I, one meeting I’d walk in and you’d have 12 people around a boardroom and it was very austere. And the other meeting I’d walk in and we’d break casual.

It was like, and so different in that sometimes I’d come in and they would just start asking questions. They wouldn’t even give a chance to do the pitch. And other times you come in and do you do the full pitch and sort of the formal. And then they start asking questions. So really we learned, or I learned that you have to match what who you’re talking to and follow their leads.

You can’t walk in and just say, okay, let me do the pitch and force them in that pattern. Every investor is different and they sometimes have different styles and you have to match their styles as well. Now I know it’s different than when you’re pitching on a stage. That’s, that’s obviously you’re doing your pitch on a stage, but we’re actually going for the dollars are in [00:17:00] that boardroom, the meetings are very different.

From meeting to meeting, have you felt, have you seen that any stories you can share about. Yeah. I’ll tell ya. I had a unique opportunity out in SF that I met with two guys from slow ventures. Sam lessen was one of them. And this guy was an early Facebook guy. He was the guy who took Zuckerberg around with it.

It was his dad that got Zuckerberg, the early financing. And then he went off and he built his own business. Sam did, and then Facebook bought his business so they could get Sam in Facebook. This guy’s so freaking brilliant. Like you’re in the room and you see his brain working. It was just amazing.

And the questions he would ask you. Unbelievably deep, like quick just all of a sudden, like, how are you thinking about this? And it’s oh my God, so deep you’re floored. So yeah, w when you do those, [00:18:00] one-on-ones, you have to be quick on your feet. Anything can happen, the more you can put yourself in that situation, the more that you’re going to grow as a human being, and the more you’re going to learn, which is going to make you better for your next meetings, right?

Like all your IPS, Collin, have prepared you for every one of your businesses, to go to the next one. Yeah, absolutely. And the last thing I’ll share about that process that I went through there was that, we did I think it was only about seven or eight meetings in the U S and about 30 in Canada.

We closed three institutions in Canada, three in S. And why do we have such a higher hit rate in the U S because when we went into the U S we specifically targeted RBC had set this up. We targeted technology by technology investors. And in Canada, a lot of the ones that are generalists they tended to invest in, everything from oil and gas to technology.

And we just did not have a high success rate. So [00:19:00] who you pitched to can almost be as important as how you pitch and the quality of your pitch, because you really want to be pitching to the investors who invest in your type of company. Yes. A hundred percent. And you bring up a really good point because be prepared, like most people pitch to get investors.

They pitched to 80 people. So you’re going to pitch a lot, you pitch for pitch competitions. That’s one form of pitching. Then you pitch. Two investor groups like it’s Friday, right? So on Monday this week, we’re because we’re closing our round. We pitched on Jason, Calacanis says launch syndicate.

And so cause at the 10,000 people, and then anybody who’s interested, then they have you do a zoom presentation. So you’re walking them through a deck and talking about the product. And then you spend, we spent 31 minutes answering questions. We have 25 questions that were two and three part questions, your growth on the [00:20:00] spot.

No prep. You gotta answer it. You can’t think about it. It’s gotta be natural coming right out of ya. And so there’s all forms of pitches that you do, and look, we’re here. A lot of people that are in the room today, we’ll answer some questions for them. If you want, we can open up and start going down through the question.

Absolutely. Jeff, do you want to manage the room today? Shelly, once we bring people up. Yeah, I have a question. All right. So we have this great idea or so we believe we do, at what point, like what are some key tips that you can give, members here on, when is a good time, I’m jumping ahead to start preparing that pitch and you’re actually ready to raise money because I think, it seems like it varies a lot.

Like you’re a late much later stage. You have a very commercially viable [00:21:00] business software Lil, but a lot of folks here in the room, probably they’re still at the idea stage, and maybe they need money to build, an MVP. So I’d like your thoughts. The different approaches and your suggestions, you bet.

And great question. So it brings me back to the, I started I did a scorecard before I did this business and because I had exited my last business, which was manufacturing. And it’s easy to happen, stance, get into your next business, right? People offer you opportunities and this and that, or you buy, an ongoing concern or a turnaround or this or that.

So I did a it’s like the old saying, everybody looks good at 3:00 AM in the bar. So I did a scorecard and said, okay, really what I want to spend my next, 10 years doing. And on it, I put all the things that were important to me. And so what was important to me was I love small business owners, so I wanted to help and impact small business owners.

I wanted to build a technology first company because I love technology. I wanted to scale it to a [00:22:00] hundred million ARR because I wanted to build something that was going to have a legacy and just be really big. And I wanted it to have VC backing, venture capital backing. And I wanted to reshape an industry because I was in manufacturing and I was sitting on the other side of the table, just getting bludgeoned by technology, sitting on the door.

And changing the industry. So I thought it’d be much more fun to be on the other side of the table. So I would say to people that are thinking about, their business don’t do anything for money, because if if you do it for money, you’re not going to be successful because if that’s your driving motivation, that’s not a big why you’ll give up when it gets hard.

So really understand what your, why is, why are you doing what you’re doing? I love building teams. I love bringing great people together. So that’s my why. And I like solving problems. Understand your. Then go to your circle of advisers. And if you don’t have a circle of advisors, find people that you [00:23:00] admire and trust, as Michelle was asking me this question, I remember sitting at the Metro diner with Collin saying, yeah, this is what I think my next business is going to be called.

What do you think? You think the time’s right? Here’s it. And call him Colin grilled me and we went round and round about it and he’s I think he got a winner and this is when the business was on paper. And then besides Collin, I talked to another good friend of ours, Oscar who I know can rip apart any business.

Cause he’s done a ton of tons of due diligence. And I spent four hours with him one night for him to rip it apart. And at the end of it, he said, I think you got a winner. And so when you go and you do that with some of your trusted advisors and if and listen to what they say, don’t be defensive. It, nobody likes to hear that they’re babies.

But if everyone is saying your baby’s ugly, then rethink, maybe you got the wrong partner to have, pretty baby. So figure it out. And maybe it’s a few tweaks to the business that then, and then go back to those same people and say, Hey, what do you think [00:24:00] about it this way? Because get that whole in first, then go ahead.

Oh, I, so what I love about your business though, is two things. One is you’re solving a big problem for small businesses. Accounting is expensive. And the fact of the matter is if you can drive down the accounting costs, you can actually help more small businesses succeed. It’s pretty awesome. What you’re doing second it’s recurring revenue.

You’re making a monthly recurring revenue and for you, it’s all about growth and subscribers and cost of acquisition. And those are the models that work really well. So I do think it’s a very cool business. Thank you. Thank you. And I love the fact that yeah, we today we got the most amazing review from a customer that wrote in and told us from the onboarding to the accounting, to our customer portal and UI and UX of it, we never get a review where they like hit from beginning to end.

Usually it’s just one piece that resonates with them. So thank you for saying that column and yeah we love helping people. [00:25:00] When you’re taking an idea, do your early work, once you’re in and you start taking other people’s money, that’s a huge responsibility. So you owe it to yourself into an all early money is typically friends and family.

So you’re taking people’s money that you love. So do as much of your homework ahead of. Try to look for the barrier, why your product will fail. Like I, when I did this business, I said, the product will fail. If the timing is not right, that people will use somebody that’s not right in their backyard to do business with them.

So I went and I did trade shows, it cost me whatever the money was out of my pocket. And I did trade shows outside of the area to prove that I can be customers. So figure that part out. Does it long way to answer the question, but hopefully it answers the question, Michelle. Great. Thank you Lil and speaking about helping people, we’ve got a bunch of people who came up on stage, who I think have questions for you or one help with their own pitches.

So we’ll start taking questions from the people [00:26:00] on the stage. And as the stage gets crowded after you’ve asked your question and Lil’s had a chance to answer, we may move you back to the audience, but go pal. Thanks for your patience. Did you have a question from.

Go pal. If you’re there, unmute yourself, go. okay. Let’s go on up there. You are. Go ahead. Did you have a question for Lil about pitching?

Okay. We’re going to go on to the next person, cause we don’t hear you. Sorry about that. That welcome to the stage. Did you ever. Yes. Hi. I’m so excited that you guys made this because I’m so nervous. I’m going to pitch for the tenants incubator with grant Cardone, his team coming up, and I’m super nervous because I’ve never done anything like that.

I’m the type I’m like the unicorn like Brandon Dawson said is there was always, there’s always a unicorn. [00:27:00] You got to know who the unicorns are. I’m like you in a sense where I like to think of different ways. Solve problems for people. And I, and it’s it’s, it seems like it makes so much sense.

And like for instance, I went to an appliance store over here by where I live and the guy in the store he’s about to close the store down because the owner he’s 80 years old and the guy who was working behind the counter is Maybe 60 or 70 and I’m like, no, don’t close it down. Just figure out a way to, you need an exit strategy.

All you need to do is get some kids in here, midterm part of it into a camp and then teach them how to fix stuff. And then you can hire somebody for the back, for the back or whatever. And I gave him some good ideas. We’ll like the landing page and like getting just like before he invested in.

So like doing a whole bunch of stuff, just maybe just getting like the email list and everything like that. So then after I finished talking to him, I said, oh, maybe I’m an exit strategy. I’m strategist person. Maybe that’s what I need to do. Did you have a question about perfecting your [00:28:00] pitch?

Because we want to try that. Yes, I’m trying to figure it out. Oh, okay. I’m sorry. I veer off sometimes. So I was trying to figure out, like, when you’re trying to make a pitch to someone to like, how do you do you guys have like shortcuts, like templates or a book that you can use as a newbie to this?

Yes. So my very first pitch that I was doing, I did the guy case Kawasaki 12, 12 slides for a pitch. So you can start with that and then you can, you can, Google tech crunch has a lot of information on pitch decks, has a lot of information on pitch decks. And also the other pieces is you gotta, you have to identify what your business businesses is it a SAS, isn’t it a tech enabled SAS?

Is it a marketplace? Isn’t a product business. So that’s very important that your pitch deck is going to show what your, what type [00:29:00] of business, because investors put them all into categories. Oh, that’s marketplace. Oh, I don’t do marketplaces. I do pure SAS, are you, ed tech are you’re, prop tech, those types of things are important.

Any tricks for nerves, like people who are like I relate to that bad. I think we all do, just not one minute before you go on stage. And like you talked about, the, I can’t remember the name you used for the power stance and the 6, 6, 2 minutes and all that, but is there. Other tricks.

I know for myself, I try to take a very deep breath and then I, and I calmly just take that breath. And then I come on stage and I try to start calmly because I know often when we get on stage, we speak too fast. And we, that nervousness comes through. But any other tricks, maybe Jeffer Lil or Michelle, to deal with nerves?

Sure. Jeff, Michelle, you want to go first? I think you’re up first. Here’s Joe. I think [00:30:00] breathing is really good. Sometimes it helps to just focus on one person in the audience if you’re on a stage and think about talking to one person if the size of the. Makes you nervous. So if you’re unnerved by walking into an auditorium and seeing 300 people out there, don’t look at the whole crowd hone in and then don’t stay with that person.

The whole presentation move from one person to another person, but keep your focus on a smaller group or individuals, as opposed to the whole room. If that, if seeing the size of the crowd nerves you a bit. And I remember once going to, and we had almost no one in a crowd once, and it was like six people, eight people.

It was a dying convention. And Jeff said, just pretend. There’s a lot of people in the audience. We’re going to fill them anyway. And you’d never know who’s in the audience and you have to give your hundred percent on every pitch. You never know, don’t assume just because there’s two people in the audience or there were jeans or whatever.

You’re not going to raise that money. You’re not going to have [00:31:00] that big break it’ll happen. And that’s interesting. It’s the reverse that, Jeff could see it in me. If I get a really small audience, I get, oh, he gets so upset and then, but really it doesn’t matter. It’s you just give it your all, no matter what, it’s such a great point, Kahn, and there’s two sides to that coin.

One is absolutely right. You never know who’s in the room because at the end of the day, if you watch the, we crashed the series on about about we work. One of the interesting scenes was when Adam Newman goes to Japan to give a presentation he gets himself one stage in front of a room of a hundred people or more several hundred people.

But he was actually giving the speech to one person in the room. The only person he cared about hearing him was Matsu son the head of of of SoftBank that invested in the company. SoftBank. All he cared about was him. So it didn’t really matter if there were a hundred people in the room or one person in the room, as long as it was the right person, his concept.

So always give your best pitch. And then the second thing is in today’s world, almost everything’s being [00:32:00] videotaped, right? So everything’s being shared afterwards. So anytime you’re giving a presentation, that’s going to be recorded. You have to give that presentation like on your a game. Like you’re giving it to a stadium full of people because people are going to see it after the fact.

And I’ve seen people make the mistake, they get up on stage. They make a comment, oh, there’s nobody here. It must. Everyone must have been out drinking late last night, Jay. I wish there were more people here and that’s all going on the recording. So now when people watch that presentation on YouTube later on, they can see this person dejected and low energy instead of seeing an amazing presentation.

So it doesn’t matter if there’s an empty room. If there’s a camera there or a handful of people in the room, as Colin said, you always want to give your a game. You always want to give the best presentation.

Yeah, and I would just add, look, it’s completely natural to be a little nervous and I don’t think there’s anything wrong with it. I think the key [00:33:00] here and Lil, by the way, I think you’re really good at this is just like getting out of your own head. I find if you smile and, like call and said, take a deep breath, just like those little things will take you a long way.

If you’re super rehearsed and you really believe in what you’re talking about and confident it will come through, it’s okay to be a little bit nervous, slow it down and smile. Some like people appreciate that. They’re just looking a lot of times for that human connection. And when they’re investing, yes, amazing to have the most amazing idea and is perfect and everything else, but they all have.

A big part of it is they’re investing in that person. They’re investing in the team. So it’s absolutely critical that they have the trust and the rapport. Thank you. So let’s take a few more questions from the people up on the stage. Guarani I think you’re next. [00:34:00] Welcome. Hey Jeffrey, thank you so much for giving me a chance to talk.

I don’t have any specific question, but I would love to pitch to the audience and have have you all just totally dissected. I don’t know if that if the time is right now or no, it’s fine. That’d be fine. That’d be really fun to do. So let’s give you puts to put this on the clock though.

But what about, can we do this in 60 seconds or less? I know it’s a mini pitch. Okay. But are you able to do that score off or we do need a little bit more time. Maybe two minutes. Alright. Two minutes on the clock. I will be recording on my phone the two minutes timer, three, two, one go.

Perfect. So before, before I go into the fridge real quick I’m getting ready to pitch investors. And what I’ll walk through in the two minutes is the story for the pitch to Lynn’s point like now, how do I hook the investors onto something? I’ll just get started now. Hi [00:35:00] I am gone off I’m the co-founder and CEO of Tangela.

We help companies build engaging and intuitive employee onboarding programs. Before I go into the pitch will love to share an experience of the time when I joined Glassdoor as a new hire. I still remember. I was so nervous before joining my day. One came in, I went into. And I got this amazing warm welcome from my team.

That welcome, helped me settle my nerves over the next few weeks, I got to meet my leaders. I got to hear about the mission, the vision of the company I was sitting right with my team. I could throw any of your questions at them. They were smile and answer back. I built so many meaningful relationships over coffee in the corridor.

All of these little things, help me understand what Glassdoor was. And more importantly, what was my role within Glassdoor? The world is a totally changed place. Now companies are hiring remotely, internationally in [00:36:00] different time zones and distributed offices work from anywhere as the new normal.

Can you imagine what the employees go through these days, but their onboarding one, do you have to put it really well? She said, it feels like I just closed the laptop of my previous company. And I just opened the laptop of my new company and just stop behind Gmail and slack, not knowing what to do at times.

If I have a question after do a bunch of back and forth on email and I don’t even know what, how the person on the other side is perceiving this back and forth will think I’m dumb. At times I questioned whether it was the right move for me to actually change the company from a company point of view, this is a big problem.

They’re going and getting so many new hire spending so much time, energy. And if they can’t make them productive, worst case of the new hire leaves, that’s a big problem. Companies know that at, and that’s where they are. Okay. Taking a chance on a startup like us, just to give you a sense. We went from almost no revenue to north of [00:37:00] 300 K in annual revenue, just in the last eight months with no marketing, no advertising, mostly just SDR.

What we do is really simple. We help companies become intentional with their onboarding. We take their onboarding that they had and put it in a digital medium . Okay. So we have the two minutes. Perfect. And you had the opportunity within that two minutes to try to deliver your pitch. And I know we set tight rule up here for you two minutes.

So it felt like you spent a lot of time talking about the problem and the why, but not really the ask does that often happen Lil in a pitch time just runs out and you haven’t even been able to make your ask. Yes. So yes, here’s the thing I wrote down, like early on in the pitch. So your headline is that an eight months you’ve grown to 300,000 net your headline and should have been your headline.

When you said the wording before, first of all, let me congratulate you on having the courage to come in and [00:38:00] stand up and to do your pitch. That’s tremendous. So first and foremost let’s recognize that when you launched into your pitch, you said before I go into the pitch, I would love to you started out saying what you did and then you go B, those are all unnecessary words.

I don’t need to know that. Just you could have said, we do this and this, and then you could have said, instead of say, before I go into the pitch, let me do this, just launch into it. I worked at glass door prior to this. When I joined the company, they had the most amazing onboarding experience.

That experience is what many tech companies have, but other companies don’t have. We have solved that problem. So every company can do that. And in eight months time, we’ve gone from zero to $300,000 in revenue. This is a huge problem for companies and one that need to be solved. The pandemic has accelerated this problem because people feel that they can’t put a face and a name together, and they feel stupid oftentimes, or not that I wouldn’t use the word stupid.

They feel oftentimes in [00:39:00] their silos that they don’t know what the other person is feeling because communication is 85% non-verbal we solve this problem, blah, blah, blah, blah, blah, some kind of close. And you do normally ask for the amounts you’re raising and your evaluation is. Yeah, you gotta be careful with that.

So it depends. Some environments allow you to put that in some environments you’re not allowed because it’s against some kind of law. When Jason Calacanis is pitches, when he would put those on video across, we weren’t allowed to to put what our ask was or what our evaluation is.

You can say we’re raising, sometimes you can always say so. So what you could say in this situation, and I’m sorry who’s named this was, but what you could say is we’re raising our pre-seed round. My emails such as such on I’m CEO and founder of love to talk to you.

Yeah. And one thing I would add too, if it’s okay, Quora when your testimonials are great [00:40:00] and they’re really. Powerful when used effectively, but the testimonials should be of your solution, not of the problem. So when you were telling your pitch and your story you had, you told the story of a woman who complained about how PR how trouble troublesome it was when she switched from one company to another.

And the computer was the same, but that was a testimonial of the problem, but would have been much more powerful is a testimony of the solution. So someone from an HR department of a company, who’s using your service saying something, w our employee satisfaction ratings, since we started using this onboarding process have gone up 150%, that’s going to be much more powerful than someone telling us what the problem is.

Totally agree, but. Yeah, th there’s an easier, more succinct. And but T and know what your headline is like, they want to know you, you’re obviously you have traction and product market fit because to scale with 300,000 in eight [00:41:00] months as big

love, love all the feedback. Thank you so much for the feedback. Jeff, do you have a show that you run on Monday nights? Yeah, Monday nights Sharon cognac, and I do a show it’s not pitching as much as it’s the brand story, but a lot of the elements and advice is the same. So we do this Monday nights here on start-up club at 6:00 PM Eastern, and you get three minutes to tell your brand story, and then we give feedback on the brand story.

So it’s leaning more towards your brand story than the actual pitch, but there’s definitely some overlap between the two. So if you’d like to. To check it out. Please do come on a Monday night and Collin, maybe we should do one. We should do a session where we’re just doing pitch after pitch one minute pitches.

I think that’s a great idea that you advertise everybody does. And then we give 30 seconds feedback. Boom boom. Now, and that everyone should bring their resting pitch face. [00:42:00] Yeah. The way that you had Jeff Dyke, like dissected Europe’s pitch was insane. That was really well done. Like I was really impressed.

I learned a lot. Yeah. Yeah. So let’s go on. Thank you. Gora thank you for sharing your pitch. Hopefully this feedback was helpful. We want to try to get to everyone who’s still on the stage. So let’s go to Ming’s. Next means. Do you have a question for Lilla? Do you want to do a really short, I have a question for Lil.

So my question is, can you talk a little more about the follow-up after a pitch to an investor? That what the process like? Yes. Great questions. So depending. So if you’re doing a pitch to a small group what you want to do is number one, you want to thank everyone for their time. And so if you’re pitching let’s see, like I did a pitch yesterday.

So if you’re pitching a couple of people, you want to follow up with an email, thanking them for their time and leaving the door open for future questions. But I always go for, is there going to be [00:43:00] an interest or not right after the. The thing that I people’s been saying, it’s like, if they seem like they don’t ask too many questions and they say, quote, unquote, I love it.

A usually mean the opposite. Is that true? Or are those people like worth chasing down? Okay, this is going to be this. I probably shouldn’t say, but I’m going to say So there is there’s VC speak. So it depends on the size, right? So if you’re going after a pre-seed or a seed or angel funds.

So that means that people just may not know the right questions to ask you. So you have to gauge that you have to open the door, read your audience and open your door to answer those kinds of questions. Do you have any questions? What area, tell me, an area that gives you pause or tell me what you really like about the business.

Tell me, do you think you’re going to invest or not invest in Y always try to get the why, if they’re not investing that’s important because that’s going to give you feedback that either you’re not conveying the message and the proper way to get it across to them, for them [00:44:00] to understand, or it’s it could be a blind spot on your business.

And if you’re hearing that same thing over and over again, it may mean that you need to pivot or tweak something in your business model. So the other piece of it is that when you’re dealing with VCs never want to feel, they don’t want to close the door to miss out. So even if they think that there’s no way, but then maybe you’re that one that got away from them.

There are, I’ve been at a fireside chats where people that passed on investing in Amazon now, that’s one of their greatest regrets, right? So every VC has their greatest regret. So what they want to do, they don’t want to tell you, no. And all these reasons why no, they want to leave the door open.

So then they don’t want offend you. So then maybe later on, if they decide they still have an opportunity, for a series B or series C. So typically the questions they asked you where they’ll say so tell me how you think about whatever. So how are you thinking about whatever? And then they’ll go and then you’ll answer and they’ll go.

Oh, super interesting. Yep. Yep. Got it. Got it. Got it. Yep. That’s helpful. Yep. Super [00:45:00] interesting. And so they, it’s hard to read them because they’re going to say that to no matter what. And the only way that you can really read, if they have an interest is the speed at which they come back to you and how well engaged everybody who’s on this call today.

Be sure that you sign up for doc sentence doc, as in Charles, send S E N D 15 bucks a month and do not send your pitch decks to anybody without putting it on docksin will then give you feedback and tell you how much time they spend in your pitch deck if they open it. And what, and don’t tell you how many seconds per slide, very helpful feedback.

Yeah. I think also creating a sense of urgency. Like the train is leaving the station and, whenever I’ve done offerings or raised money I always had a deadline and I know that can be risky Lil, because if you don’t raise your money within the deadline, you can look a little bit like a failure, but any thoughts on.

But Lil got to [00:46:00] call out there they are. Yeah. I’m here. Any thoughts on a deadline, setting a deadline and creating that sense of urgency? It’s worked well for me in the past when it comes to raising money, but I wanted to get your feedback on that. It’s a hairy market right now.

Like for anybody that’s out there raising money with the market going down like it did SF is starting to tighten up. Even though there’s still a lot of frothy money out there, they are getting, they’re getting more particular about who they’re investing in. So read your market, if it’s a frothy market, then you can put the pressure on, Hey, we’re going to be closing around.

But if it is a market that’s not in your favor, which is a market that we’re getting ready to enter into. Putting a date could be tough. Because then you can’t go. And here’s the other thing, too, in that I’ve learned, they all talk to each other, just like us as entrepreneurs. We all talk to each other investors, all talk to each other and they’re interconnected through the craziest ways.

One, one question on that front is if you are not putting in a date given the [00:47:00] market what is it that you’re trying to do with the conversation? Say that again? What is it that we’re trying to do with what? So if you had an art putting in a date to say Hey, we are closing around here, is it, are you just keeping it open with the investors to say, Hey, I’m resaying would love your feedback and just keep following up with them.

Take what would be the. So Colin is saying give them a date. Hey, we’re closing in three weeks. Or we’re closing in a month, typical time it takes to close around is six months. Go out and start doing what you need to do six months prior to actually needing the money. If you can close it in two months, three months, four months, you’re way ahead of the game, but you’re going to, just settle into that.

You’re going to need to talk to 80, to a hundred people. I create a spreadsheet on the spreadsheet. I put, who they are their VC website, who I’m talking to the results of it who introduced me and I keep all of that information. And then if they come back and say early for them, are they a potential for [00:48:00] series B or series a or what round that you’d be raising.

And so I highly recommend that you do that. Just tell him, just say, Hey, we’re, it easy, a safe thing to say is we’re just at the beginning of starting to raise our round.

Great feedback. And thank you for that question. And before we go to Rowan, I’ll just add one thing that I thought of while you were talking, though, don’t stress over naysayers. When you’re giving your pitch. If you’re doing a pitch in a room and there’s one person who’s very negative, don’t necessarily tune them out and don’t treat them noticeably badly because they’re being negative because oftentimes at least in my experience, the person who’s the most negative in the room will turn out to be the most positive person.

And we did a pitch when we were raising money for bar point in New York city with a big firm. And there was one of their executives who was just sitting there with his arms, crossed, shaking his head spaces, [00:49:00] grunting and groaning throughout the whole pitch. And in the end, he turned out to be the one that made the deal happen.

So you never know what they’re really trying to signal you. Yeah. I don’t know if he’s ever happened to you. If that’s her beating you up, it could also be a buying signal, right? If they’re not engaging, if they’re not asking questions, if they’re not really digging in deep, if they’re not asking about every potential risk, that’s a bad sign.

I think it is good when at least if they’re engaged, you’re going down the right path generally. Yes. Yes. Awesome. We have a few minutes left. Let’s try to get to row hit. And then Elizabeth, they’ve been waiting patiently. Rowan, did you have a question for will grow it? If you’re there, tap that little mic button to unmute yourself.

There you go. Yeah, I know I have anyone. Yeah I have a question but not to. Actually I being man, [00:50:00] sorry, but if it’s not related to pitching, I’d ask you to save it. We really want to stick to the topic. We brought Lil on to share her expertise in this area. Elizabeth, did you have a question for, will Elizabeth go ahead and unmute yourself there.

If you have a question, there you go. Yeah. So I have a couple of questions, but I’ll the first one. Is, has anybody ever tried preparing for the pitch by holding the audience in mind while practicing compassion meditation?

I haven’t, but that sounds pretty good. I know I was like, I don’t even know what that is, but if you know what that is, maybe you can share with us. Oh, compassion meditation. There’s it. Look it up. Richie Davidson the Dalai Lama. Everybody’s got a great way to do it. I’ve got my own. But my other question is Lil, can you put DocSend or whatever that was in the chat.

So we use it. Sure. Our or [00:51:00] Michelle or deaf can one of you guys. I don’t know where I’ll do it. I’ll do it up there. I put this on, do up there. Anybody wanted to learn more about your company? So put it in the blog and the show notes. It’s awesome. Yeah. So it’s D w So in a few days into mid next week, check out the.

No show notes to recordings and we’ll have the resources that Lil mentioned. The problem with that website I found is that it doesn’t comply with California privacy, net privacy law. That which requires that you have a button that says, do not sell my information or cookie preferences, you can opt out of undock.

It says the startup club startup or whatever startups. That’s great feedback. We’ll Michelle will take that and [00:52:00] add that mixer that’s added. It sounds great. I really appreciate that. DocSend is It’s owned by Dropbox recently. They bought it. But it’s awesome. It’s an awesome tool, and that’s the thing you need to have the greatest.

That help you. I’ll give you guys another tool for today for people who are out raising mercury bank has a section on their bank that they give you all kinds of Intel on VCs. Can you put that in the chest? Okay, so now just for that one. Yeah. Yeah. I want to remind everyone that we are recording.

We are recording this show, so you can go to start-up dot club and listened to the recording and replays it turned on. So if you didn’t take copious notes and want to refer back to anything that Lil shared today feel free to listen to the or check out the replays right [00:53:00] here on clubhouse.

That takes us right, towards the top of the hour. Lil, is there any things you wanted to share? Anything that we didn’t ask you, whether you did get a chance to share about perfecting your pitch? Just as in everything in life, there’s people who are not prepared, people who are prepared and people who are always prepared when it comes to pitching, when you choose to be a founder in a startup, it is one of the hardest journeys.

There is not to say that other journeys aren’t really hard or building any business is really hard, but when you’re a startup it, this is my first tech startup from scratch and it’s my eighth or ninth business. There is nothing like it. There’s great highs and hard lows, but just be as prepared as you can, and really know your.

I wouldn’t trade what we’re doing for anything. I love it. And then Collin, you’ve done startup after startup. In fact, when your [00:54:00] companies get too big, you sell them. So you can go back to being a startup, which is what you guys are doing right now. It startup stock club. So you can attest to this, right?

No, absolutely. And I think the other thing too is just to have fun. And I know that sounds everybody’s so scared. They’re so afraid of that moment, but then if you take that breath and you walk on stage and you just think, wow, this is really fun. Everybody’s looking at me right now. I have the audio.

I don’t know about that. I don’t look at it like that. I don’t go oh, this is fun. I do enjoy it. And I think you can enjoy it. And if you can enjoy everything in life, it’s just a mindset. And and people see that too. And I know you enjoy it Lil. I’ve seen you on stage. You love it. You love it.

Yeah. I love that. I love the challenge. I love the highest mountain that you can climb. I love all of that. The last piece I would say is that life changes in 180 seconds. So don’t give up don’t, don’t go down into a deep, low, and in three minutes time, the [00:55:00] whole world can change that best investor for you.

That best opportunity for a partnership that best, whatever it is, can be in the room that you didn’t even want to go that night. And there they are. I don’t think anyone like that, you guys are awesome. I just wanted to let you know Lil I’ll be following you and trying to get some one-on-one with you.

Cause I feel like you guys are really good at this. Yellow is so good. I can tell. Thank you. Thanks. Good luck with your with your pitch as well that we’re looking forward to hearing, hearing from you maybe on a future show. All right. That wraps it up again this week. If you want to check out the replays, go to startup doc club or you can go to your favorite podcast network and it was in the chat there.

Somebody was asking, cause there’s a number of podcasts called serial entrepreneur. You have to search for serial entrepreneur club and that’s the actual official name of the show. So search for that and you can listen to all of the podcasts we have over [00:56:00] 55 now. And we’ll see you again. Next Friday, two o’clock Eastern on the serial entrepreneur club podcast, clubs show and podcast link.

Thank you. Bye guys. Thanks will thank you. Thank you for organizing everything. Thank you.


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