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May 9, 202452mEpisode 41

How do you go from a dot-com failure to two successful exits?

The short answer

After a dot-com bust wiped out his first company, Shane Neman bootstrapped two businesses to successful exits, including an SMS platform he grew to nearly $15M in ARR. Now an active investor, he explains why founders must prove they don't need VC money to attract it and reveals the provocative questions he uses to test their resilience.

Market Context

What 2026 exits actually pay for SaaS

Miro had $600M ARR and 250,000 enterprise customers. They sold for $1.79B — roughly 3x revenue. Their 2021 investors took a 90% haircut on their mark. This is the current market clearing price for quality horizontal SaaS. If you are building toward an exit, you need to know which multiple category your business belongs in — before your board does that math for you.

Highlights

  • Grew SMS platform EasyTexting to nearly $15M in ARR before its 2013 sale to a strategic buyer.
  • Bootstrapped his second company to over 100 employees and high tens of millions in revenue after his first VC-backed startup failed.
  • Seeded a DTC company that grew from $40k to $4M in ARR in one year after the founder hit the milestones he set.
  • Warns founders that venture is a 12-year game, not 7-10. A 6x paper markup is 'imaginary' until there's liquidity.
  • Tests founders with provocative questions: 'You had two failures before. Why should I believe you won't fail again?'

The full breakdown

Shane Neman’s entrepreneurial journey began with a painful lesson during the dot-com bust. His first company, Offix, was an ahead-of-its-time SaaS business that failed after VCs pulled their committed capital. Jaded by the experience, Neman bootstrapped his next venture, Joombug, a vertical SaaS platform for the nightclub industry, growing it to over 100 employees and "high tens of millions of dollars in revenue." Recognizing the decline of email marketing, he built an internal SMS tool that he spun out into a new company, EasyTexting. Neman ran both companies side-by-side for a year before selling Joombug to focus exclusively on the SMS platform. He grew EasyTexting to nearly "$15 million in ARR" before selling it in 2013 to a strategic buyer. This experience shaped his core belief about fundraising: "VCs want to invest in businesses that don't need their money," he states. He advises founders to build a position of strength, arguing that in the current environment, the excuse of needing capital to build is no longer valid. "You can build anything without money, pretty much," Neman asserts. Now investing his own capital, Neman looks for coachable founders with game-changing ideas. He cites his seed investment in Allermi, a DTC allergy spray company. The founder initially approached him with an idea but no traction. He gave her specific milestones, and she returned a year later having hit them, growing from "$40,000 to 4 million in ARR" in the following year. Beyond metrics, Neman tests a founder's character by asking intentionally difficult questions to gauge their reaction. "You had two failures before," he might ask, "what's going to stop you from failing again? Why should I believe you?" From an investor's perspective on exits, Neman is pragmatic, cautioning that venture is a long-term commitment. "Some people say it's a seven to 10 year game, but it's really more like a 12 year game," he explains. He points to his investment in Figure AI, which saw a 6x paper markup in just one year, but emphasizes that such gains are "imaginary" until there is a liquidity event. This patient, realistic approach underscores his view that successful outcomes require resilience, a strong business foundation, and the mental fortitude to withstand frequent losses.

Who's on this episode

Shane Neman
Shane Neman
Founder & Manager · Neman Ventures

Shane Neman is a serial entrepreneur and early-stage investor managing his family office, Neman Ventures. After an early venture in the dot-com era, he bootstrapped Joonbug, a vertical SaaS platform for the nightlife industry. Seeing a need for better marketing tools, he then founded Easytexting, a pioneering SMS marketing platform, which he grew to nearly $15M in ARR before its acquisition in 2013. Now based in Miami, Shane invests in early-stage companies and is the author of "Nightlife Lessons," a book detailing his entrepreneurial journey.

Questions answered in this episode

References & resources

Hosted by

Jason Kirby
Jason Kirby
Host · Founder, Thunder.vc

Podcast host, angel investor, and serial entrepreneur with 4× exits ranging from small businesses to VC-backed tech companies. Jason has been personally involved in over $100M in transactions and now helps founders close their next transaction at Thunder.vc, from pre-seed rounds to $100M exits. He coaches founders through their next major transaction and gets the deal done by introducing them to the right people in his network.

Apply to work with Jason

Full transcript

welcome to episode 41 of fundraising demystified today we mix it up a bit by having Shane Newman on the show an author a multi- exited founder and now investor of his own family office we get an inside Glimpse to the mind of a private capital allocator and what his journey was like in the early days of building his first few companies and what types of deals he's doing now and if you're looking for an angel investor Shane is your dream come true Shane shares what it's like building a during and after the dot boom and bust how he sold his first company and spun out another which he later sold as well he has spent the last 10 years investing in real estate private equity and writing his book nightlife lessons his entrepreneurial journey in The Nightlife industry Shane is a fascinating individual who's passionate about early stage investing and finding opportunistic Investments even though he stepped back from operating he's still grinding away and learning and gaining an edge for his family office as a reminder to get notified of our weekly podcast and newsletter be sure to subscribe at join. thunder. BC again that's join. thunder. BC now on to the show hello everyone welcome back to fundraising demystified today we have Shane Newman with us today welcome to the show Shane thanks so much thanks for having me Jason appreciate it no I'm excited to have you uh you have an extensive entrepreneurial background around you know launching your company in the early 2000s and you know kind of before it was cool to do you know Tech startup and kind of that after the do you know experience and then you know into the mid 20010s uh selling your companies having extensive experience and you know having that opportunity as an exited founder you know it'd be great for you to share your background and kind of how you got started as an entrepreneur and kind of where you are today uh sure uh my entrepreneurial background was pretty unlikely just to be hon well listen I guess it it it was unlikely and likely at the same time my my parents were immigrants that came here with nothing and so they were entrepreneurs and I watched them uh you know come up uh the the the American dream uh they you know came with nothing uh worked really hard started businesses started small businesses built themselves up worked uh 24 hours a day pretty much uh and did a bunch of uh they had the hustle let's just put it that way and I watched them do that growing up and you know better Our Lives um over time and so when it came time for me I actually ended up after college going to medical school um and that was the path that I thought I would go down is becoming a doctor uh it's the thing I thought I would always do I I did Premed in college I had a computer science degree because I thought maybe if I didn't get into medical school I'd have something to fall back on uh and uh but I worked uh you know during college as a programmer so I ended up making a a good amount of money and getting a little taste of what it makes what it what it what it uh entails to do that and how it feels um especially at that time knowing how to do web programming in the early n well like late 1990s um you know I was getting paid what a lawyer would get paid uh per hour essentially to do that and so what happened for me is I had a college roommate who was a friend of mine from high school he was working at Goldman I was in um I was in medical school he was partying having a good time and I was watching him make a lot of money and he came to me on a Sunday while I was studying and said what are you doing you know we can make millions of dollars let's I can raise all the money and you can create software and I have an idea and that was it I quit that day and we went on a two-year journey of raising money from people who thought it was a good idea to give 22 year olds millions of dollars uh during the do com boom and we created a company called offix which is essentially Microsoft 365 but we use Citrix to deliver apps so it was like a web portal that businesses can use to log in and you know give apps to their customer get to to their to their employees so all the Microsoft Suite uh quick books you know anything that was web based I mean uh Windows based uh they could do so essentially we had an app store we would host your files in the cloud we were a SAS business but none of those words existed uh we so we were trying to do that when no one first of all we didn't have those words uh but the second part is you know we didn't even how to describe it properly and people didn't know how to consume it because they weren't used to paying for a software on a monthly basis uh or on a yearly basis uh for that matter they were used to buying software and then upgrading so uh suffice to say that that that didn't work out after two years the.com bust happened and I left with nothing I was pretty broke at that point I ended up moving in with my girlfriend at the time and she was going to fit she was living in a dorm and I was living with her uh to save money uh and she would work at a few nightclubs here and there uh on on on off nights to make money and I would go with her because nobody need Pro needed programmers at that time either anymore because all the dots went out of business so if you can believe that uh programmers couldn't get uh any any kind of you know love at all like now you can't now you can't you know you don't let go of the best ones right because they're impossible to F so uh to what ended up happening is I started looking around me I saw that everything was kind of antiquated in that business in the nightclub business and to kind of shorten it I created a company called junbug uh which really I was really in her dorm room you know bootstrapped uh really kind of um Scrappy but ended up becoming the de facto Tech stack for all the nightclubs um so we created the ticketing systems the Marketing System the systems that they would run their nightclubs on and uh eventually what we also did was uh we had a consumer facing website where PE we we created a big email list of people who would go out uh two events and created a million person database uh monetized that database so we had the SAS business and then we ended up also doing events ourselves because we ended up eating our own dog food so I I built that business to a very large um and over the next eight or nine years uh you know we had about 100 employees a little bit over 100 employees uh you know we were doing tens of millions of dollar in the high tens of millions of dollars in revenue and then about a 2005 I realized that the efficacy of email uh was really dwindling because everybody and their mother had a MailChimp or a constant contact account so now you were getting an email not just from junbug but from the promoter the DJ the venue the their grandmother you know all of them right and so uh I wanted to cut through the Clutter and during that time blackberries had come out and texting was starting to become prevalent and so we realized that we want we need to send text messages to everybody and there was no out of the box off the self shelf solution you you know right now there's twilio right so but twio didn't exist for another four years uh and so as far as I know and I understand we became the first actual publicly facing SMS API in the United States uh after I built that but we really more focused on a MailChimp model where you would um you know a a business would pay $50 $100 a month and they would have their campaigns run through us and their contacts and they would get widgets and you know the whole the whole kind of ESP uh email service provider model uh just really took it out of their place book um ran those two businesses side by side for about a year and then I sold the nightclub business the nightclub software business and focused mainly on easy texting and took a lot of that money and put it into there and ran that for another eight years and grow That Grew that uh to you know about almost a little bit over 15 million in ARR um and then sold out in 2013 to a strategic who raised the money through Morgan Stanley and investor growth capital and I stayed on for a little bit over a year moved to Miami afterwards and for the last 10 years I've been uh trying to learn how to run my own family office at Investments so doing um real estate private Equity but my passion really is in early stage uh Venture and so I spend most of my time doing that and working with found Founders and more on the earlier side but not just Tech uh they do all different kinds of uh businesses um biotech food Tech uh consumer package Goods anything that I think is opportunistic and makes sense crypto that kind of stuff you have such a fascinating story and I want to kind of unpack a couple pieces here that you kind of you know quickly gave you know the overview but I think some interesting pieces here of one you know being on the bleeding edge of new technology and you know kind of before your time like you know imagine if the cloud was the word in 1999 you know people didn't really know what it was and trying to sell you know through metaphors and other things must have been a nightmare hence why that probably didn't work out even though it was the future and it was it's what the entire world is built on now and you were kind of the early custom to that just maybe too early and you know not the right timing with the capital markets but then going into kind of recognizing this opportunity for I guess we'll call it a vertical SAS for for nightclubs and kind of giving them their infrastructure to kind of support and grow and build their business um we're kind of seeing I guess spotting a unique opportunity in solving your own problem and then going out and build an easy texting to basically go out and solve that problem but then retain that business after you sold Junebug so just some some Savvy deal making some very you know smart Innovation uh you know happening in your career to what now has put you in a very you know I would say an envied position by most Founders that are still grinding today who would want to be in your Fe grass the grass may seem Greener but you you know the grind still never the grind never leaves actually but uh yeah I listen I it doesn't suck I won't I won't I won't you but but that's you know 16 years of busting your ass off grinding building you know a company that failed and then building a company that's successful selling it and continuing to build another company T it yeah you know you've earned your seed to to be more comfortable and get to choose what you grind on um yes that is true the the one thing that definitely I get to choose is how I spend my time and that's the most important uh thing um but you know I do choose to to work a lot still so um that's something that I think is either in you or it's not um and you know there's no replacing hard work um because you could be the smartest person Hey listen this is all cliche stuff that I'm telling you anyway so I don't need to reiterate what you can read in like every other book uh that tells you about Entre entrepreneurship well speaking of books you have a book uh you know you want to kind of tell the audience a little bit about what's in that right right here I can see so this is this is the book uh see got that um so this this book came out of me reiterating the same stories over and over again to the founders that I've been working with uh and and and I would find that the most interesting stories came from junuk to be honest because um basically I got screwed every which way you could possibly get screwed in that business because of the people that I was dealing with and the industry that I was in uh and so I learned a lot I learned I learned what to do what not to do I learned how to look at psychology of your customers um I learned how to anticipate 10 steps forward uh of what may happen um and so the lessons are in this book uh that's why it's called nightlife lessons I structured it in a way that it basically is a lesson per chapter and each chapter then also winds down with how I applied those Le lessons that I learned subsequently in either easy texting or right now how I use them when I'm investing and doing Venture um so I thought I thought that that was unique and you know I actually rewrote the book to do that um it took me about two years to write this book which is really a passion of you know a labor of love uh because not not enough people will ever read this book or buy this book for it to be profitable for me but um if it can help a few people I would love it and I've had I've got 65 Star reviews so far which is great because I don't even have 60 friends so there's no way I could have faked that uh and so I'm just really blessed to be able to be in a position to do that and it was a bucket list item for me uh which I did and I'm really proud of it at this point no it's a it's an incredible well especially pre- chat GPT days you know I feel writing a book today is probably a lot easier than it was but also kind of pulling from your experiences and you know sharing those stories so you know you kind of talk about getting screwed each and you know each and every way which you know I feel like a lot of Founders feel that way because you know it's it's your baby that's always on the line it's your reputation it's your effort and then you know deals may go south things don't work out as planned um which is the common you know experience from most Founders it's very rare that everything's always perfect in you know rainbow and sunshines and unicorns so you know maybe uh you know kind of share with the audience kind of some of your experien since this show is a lot about like fundraising and capital like what were some of the you know either fundraising or Capital struggles that you've experienced in your past um you know as an entrepreneur so you know I bootstrapped the last two businesses mainly because I didn't want to go down the VC uh route um because we had a really bad experience the first time uh what had happened was first of all we raised some from friends and family who didn't end up being our friends and family after we lost their money uh so you have to always keep that in mind if you are willing to lose those people because no matter how out of control it might be of you uh know in you know your business failing uh you can lose friends because you lost their money and and money changes the way that people interact with each other it's not the same uh after that and so that was one part the other part was you know I think we might have survived if we had gotten the rest of the money from the VCS that were not willing to continue to give us the rest that they had committed to us um and so that was a real big blow and so I was really Jaded by that uh I kind of really did not not want to deal with a VC uh again um and so the only person I would answer to Is myself um as a self-funded bootstrapped company you act differently I think you're a lot more careful and cautious of what you do um maybe you don't grow as fast um because of that uh which could be a good or bad thing depending on your situation but there there are pros and cons to each one um I'm a VC now right so I want people who uh will take my money so I don't want you to not want the money but as a practical matter I could tell you the VCS want to invest in in businesses that don't need their money they want they want they want the deals where the the the the the the business is so good and the founders are so good that they don't really even need the money but they get access to it anyway um so as a Founder you you want to be in that position you want to be in a position that your business is so good right and you're doing so well that you don't need the VC and the VCS want you so to to the degree that you can do that um the better off you are and the the the you have the upper hand um so I wanna I wanna keep on that topic because this is something that a lot of Founders struggle with especially in the early days of you know kind of building a business and you know getting off the ground and the there's the chicken and egg problem is what every founder talks about you know like I can't build it if I don't have the money um but yeah there are many businesses that go on to be very successful and never raise any formal amounts of money uh you bring up interesting points about be careful with who you take money from if you're willing to lose those relationships I find that to be incredibly Val device and it also shapes who I go out and raise money from for certain types of things because you know my context of the relationship is not about money then you know introducing money to that relationship could be complicating uh those types of relationships and that's important to keep in mind so you know now looking back so you you raised money no point0 didn't like it went bootstrapped had success now you're funding you know early stage businesses as an investor you're actively engaged in funds and you different Investments you know when founders come to you or you know just kind of share your opinion on kind of the you know do you build it they get money do you just never plan to raise money and build a certain way like what what's your advice to those Founders that always kind of complain about the the chicken and egg problem when it comes to raising money before they build something um I think in in this day and age you can build anything without money pretty much um or very very little money it's not an excuse so like you know even back then when I didn't have tools like you do now that are free like every tool you can imagine for businesses have as a free trial or they're willing to give free credits from AWS to I don't know again your email list to anything else that you want there are no code low code Solutions I'm not saying for Tech startups or anything like that I mean even for I I I had a I I backed a a startup founder recently who got a patent because he convinced one of the larger law firms to file his patent stuff for him uh for free because it was so good and that he would pay them back later so there's always a way if you're willing to either learn how to do it yourself uh and put in the grun work and the you know and like you know you can figure anything out at this point with YouTube and everything like that or uh you know look for alternate paths to get to where you need to go uh and that that's that that that may require being novel right in in your in your approach to it right so that I thought that was a pretty novel approach um I'll pay you back later but if you think that this is a re a really good patent then do it for me now because I I this a chicken or egg thing I can't get funding without it right yeah and I I'm so glad you say it that way and like I I'm much more in the camp of you should be able to get something off the ground um by convincing those around you to support you with small amounts of money or by doing yourself to to a certain degree um and you know ideally getting to maybe some Revenue before asking for for money these days I think is something that is kind of long and forgotten after you know the zerk period of you know free money for everything all the time uh and now people are having to kind of go back to basic business principles I agree I totally agree um I think I think you can do it concurrently with if you have another business or you work I'm sorry not another business if you're employed um you know you can do a side hustle and even getting a Shopify store off the ground is easy these days um you can have like AI write it chat GPD write write your product there's no excuse anymore really the the buried entry has gotten much lower but it also you know means there's a lot more competition and you have to find ways differentiate and be able to prove that you can sell to customers and it's something that I I run into often with a lot of say very early stage you know idea stage or just you know just kind of getting off the ground with an MVP is you kind of have to be willing to do anything and everything to to kind of hit those milestones and prove to people around you that you can do what you say you're going to do to acquire the capital that you're looking for 100% so kind of saying on this topic like you going to your website you have an extensive personal portfolio of Investments you know how do you look at you know investing and and kind of what's your your typical approach in particular for like early stage Ventures uh so some of it is uh kind of cliche that you've heard before it's you know you're investing in the founder you're not investing in the product but that's kind of bullshitty a little bit also because the the you know the product does it is important too um uh because you have to believe in the idea and you have to believe in what they're what they're making and um I don't have a formal process in the same way that like a venture capital firm does um first of all I only answer to myself and not other investors so that is a big um Plus for me and I have a much bigger time Horizon longer time Horizon than than a fund does because a fund has to be like five years or seven years or 10 years I can I can do what whatever I want for as long as I want and I can make as many mistakes as I want and no one will uh will will you know will scold me for it or you know you know or I won't get penalized for it I guess I'll get penalized in my wallet that that's about it uh so I'm really looking at right now things that are really kind of gamechanging uh there's like you know I see like a million AI things right now right and and you know you being a rapper around chat GPT is not going to work right it's it's just it's it's AI but it's not AI right uh and so there has to be some Edge for it there has to be something really really different and it has to be category changing um and a lot of this is is being said by other VCS but it that can also happen by changing just one critical part of an of a of a existing industry so I'll give you an example um I've seated a company called uh alery last year um and that founder shaie came to me two years ago and she had this idea of doing a nasal spray because her dad is an allergist um and he made these custom compounded nasal sprays for allergy sufferers and she wanted to do a DTC in the same way that him and hers does that right um they they they do all different kinds of prescription stuff uh she knew about me because I I I seed in another company called apostrophe which did the same thing but for der Dermatology or for acne or te or those types of things and so she came to me and she um told me her idea and I thought it was a good idea but I thought it was way too early uh she had she didn't have any Revenue she didn't have any data to show that this spray is better than other things and I said look get to these Milestones I'll also introduce you to another friend of mine that's a VC and let's see where you can get and she worked for another year like that um and then she got to you know like 30 or 40,000 in ARR uh and the reviews were amazing so I don't suffer from allergy so I didn't really understand it but then I got to know it and then and then you know she had some more data and that's when we realize that we have something here um and so if you you know the allergy space is I mean there's big Pharma that make makes uh flones and makes like afron and makes all these things so like who is she to go and kind of disrupt that right um anyway uh she did it she she really she really has done it um she you know her uniqueness was not to go against them but to use the current prescriptions that are available three four of them and formulate different titrations based on your symptoms and so they have like you know I don't know 100 different formulations of these four different active ingredients and they custom compound it and they uh you know they intake you with an asynchronous uh tele medicine consult with a uh a a with an allergist that's in your state and then they figure out which which one's good they send you a free free one you you try it and then you go on a recurring Revenue prescription right um you know they owned this year with 4 million in ARR from 40,000 to 4 million right um and that's a success story that's that's the kind of su that so that we we ended up funding them by the way uh we did about a $3 million seed round for them um you know in January of last year and now they're doing their a round and they're getting like you know they're getting a lot of attention right from from Big VCS so that's how I think about it um she she didn't like reinvent the wheel she didn't reinvent the wheel but she made the wheel better here significantly better right with to the tune of 6,000 five star reviews of her product right and so um you don't have to be like creating something that no one else has ever created you can just do things better and do it in a unique way that makes you stand out and so that's what I'm really kind of looking forward looking for in a uh an adventure um and you know the the fact that she actually listened and she was coachable and she came back a year later with like exactly what we asked her for I mean how many people do that I mean I'll tell you I was on a on a call with a Founder yesterday and I said listen I don't really know much about your business but I have four friends that do and if you send me an email a separate email with a little you know a blurb and a you know your deck um I'll forward it and then the founder replied to my original email with all this extra stuff and you know put the blurb and then put you know attached it and then res sent the email again said I forgot to add this and I'm thinking to myself does she really think that I'm going to like recompose her email and send it to at least four people like I asked her to send me an email separate you know it's like simple like this right uh I just knew immediately that I I could just never do do do anything with this found it right so um I know it sounds like petty and stupid but you get you you know immediately who you're dealing with when you when you uh see things like this right so that's uh that's an interesting point and I think a lot of Founders just they're just so wrapped up in the execution of the business and like the thought process of like why isn't everyone a believer in what I'm doing um and that very specific example I would completely agree like if you have to make it stupid simple for the other side as like a as a Founder it's your responsibility to make things easy for those that you're train to convince to give you money or buy a product whatever it is so uh I think it's completely reasonable to to use that as a judgment factor in what a 10e plus relationship might look like yeah if they're not able to to kind of accomplish very simple things and make them easy for you so that's I actually I actually ask questions that are designed to piss you off um and I want to see how you react how does that go sometimes I curious what's an interesting story for that what happened to me a few weeks ago um the the the founder got combative and I just said to him listen I could be nice to you or I could be kind if I was nice to you i' just say oh thanks so much thanks for your time have a nice day and I'd never call you back or email you back but I'm going to give you some feedback right now your presentation sucks your attitude sucks your this sucks your that sucks and you need to go back to the drawing board and you know I'm going to ask you questions that you're not going to like and you need to keep your cool because that's it's not going to work it's not going to work like I don't need you you need me right and so at the end of and I I I don't mean that to be like a dick I'm I'm I'm just I'm being that like like that's all VCS right they don't have to deploy money if they don't want to right um and by the way like like I'm the only one who would probably tell him that the other guys will just be like I don't you know they're working for a vent Capital firm they don't have time for this yeah it'll be nice and respond again and they'll they'll never respond they'll never respond to you again so as a practical matter um it's important your your bedside manner is important let's just put it that way right it's just as important of how if you're going to raise money right if you're not going to raise money you could be however you want you know what I mean but if you want to raise money then you need to play the game I like that if you need to raise money you got to play the game and that game in particular in the points we're talking about here is like it's really like I would say the common denominator here is building good relationships like being combative and defensive over simple questions of a get to know you meaning are clear signs of what the relationship might turn into down the road um and it's it always is fascinating to me when founders get combative um so go go to go to specifically maybe an example like what what's an example of a question you ass with the intent to kind of see if it RS them up um well this one had like you know two failures before and so I said look you had two failures before what's G to stop you from failing again why should I believe you're not gonna fail again you know and that that that pushed a button and then you know I kept on pushing him on that on that subject um so you know or if if if someone doesn't know their numbers I I will push it into it you know and you know they'll get upset at that point because they they don't know the they don't know they don't know the answers right that's another thing if you you should know your numbers if you don't know your numbers of your business you shouldn't be a Founder um and well what I think is interesting is when founders try to lie so they they don't know their numbers and they try to make up that they or like sound like they do know and then list a number and then whenever they actually do pull the numbers in diligence and it's not matched up that's pretty much a deal killer in so many ways and Founders really hurt themselves um but I think there's are good kind of questions to qualify you know who the founder really is because just listening to a pitch of course that's the polished you know presentation but in reality like once you write a check there's a lot of back and forth there's relationship building there you know an extensive uh relationship there and so it's it's important to kind of feel I feel to ask these types of questions so so good insights to be sharing to Founders to be ready for this type of stuff and be able to mentally prepare for meetings to come with that intent in mind yeah um that's the other thing is like if you're coachable that's the best part if you actually like listen to advice and you take it and you do it that sounds so simple but not so many people don't do it and it sets you apart something want to ask you as you know like you would be essentially like what a Founder would put in their head like oh Shane seems like the perfect angel or like you know this it'd be awesome to have Shane as an investor um if I could just get in front of Shane he would totally in you know everyone thinks that you know um how how do people get in front of you and does it make a difference in how you make your decision based on how they get in front of you um well listen obviously if it's it like I'm human right so if it's brought to my attention by someone I know personally and I respect and they're sending it to me um I'm going to obviously look at it differently than if you cold emailed me but you know um I try not to have that bias uh easier said than done uh just to be honest with you uh but I read every email that comes through my website I don't I I'm very different in that in that matter sometimes I get a lot sometimes I go weeks without it uh but then sometimes I get hundreds of them um so it it may take me a while to get through everything but I respond to everybody even if it's a no uh I just feel like you know you went through the house of doing that with me I should have the respect to do that tell you know back back back um and to the degree if it's not for me and I have someone that it is for I'll I'll share it with them um so I found that to be helpful for for for Founders um but look um I think what what people don't what what other Founders don't realize is that this is a marketing game also so you got to use marketing tactics and so you have like the first two sentences to get me my attention and if you don't do it in the first two sentences in the subject line then likelihood is I'm not going to look at it right I'm going to pass on it because it you know I have like other to do and I got a lot of to do and so I have to like make decisions quickly and H how do I do that you know I read the first three four five sentences maximum maximum five right and I I I immediately know if this is good or bad right and so you have just about it that much time to concisely and completely tell me about your business as as as a tactical matter if you can't do that you're like not you don't know your own business or you're not running or you're not running a running a business that's you know fundable in a lot of ways well or yeah or maybe your business is you know isn't good it's like too many things or it's like you know it's too complicated or it's you know that kind of thing you know um I think you know Founders really need to sit down and think how do I explain what I do in two sentences and if you can do that first of all you can sell you you need to be able to sell your product or whatever your service so you need that anyway regardless right uh to to actually sell the product to customers uh then you need it to R fund fundraise right so the better the pitch in the first two sentences the more likely you are to do that do you find in the kind of like you know whether it's cold email or you know a referred email like in those first couple sentences what usually is stuck out to you that clicks for you is it because everyone's got their you know kind of preference sometimes it's like the the quick pitch on whatever they're doing some focus on traction some focus on how they know you and trying to connect the dots like what what do you think usually works for you uh what usually works for me is um exactly what you do in one sentence and then some stats I want to know quickly what it is that I'm looking at so can I figure out what you're doing in one sentence and can I see how what your traction is the other of oh I know this person who knows you or kind of thing anyone can look that up online right like you can just go look at my like then find someone that they have knowing thing or you know I don't know go look at my crunch based profile and look at another company that I'm invested in fact this whole thing of oh I saw you invested in this so I thought you would like to invest in this and mine is totally false like I already have exposure to what you have what you're doing so why would I want to invest in you like it makes no sense unless you're doing something completely different that will obliterate this other company that I'm uh you know invested in I mean how many you know how many companies that do the same thing am I going to invest right well and also again I'm sure Founders think like oh no we are the ones that are gonna blow them out water yeah yeah um yeah I actually think that's counterintuitively wrong right you you may not want to go after the people who invested in your competition because yeah no I completely agree it's it's usually The Blacklist for me in terms of sharing your deck and who you send information to they might understand the market but there's very few funds that invest in competitive or you know very similar products mainly because they're focused on you know diversification across different sectors but I I want to kind of switch up the the conversation here and you know we're talking about how to get into deals assessing deals but something that's often not talked about getting out of deals making money actually generating returns yeah what's some of your you like what's been some of your stories or experiences on on that front um from your investment side so I haven't had an IPO well no actually I did I had one IPO this year uh so that was but you know you still don't get liquidity because you're locked up for six months so um we'll see it so far if if things stay good uh I may end up doing really well and that it was a biotech iplo that that that happened for me um so there's different ways to get liquidity one is through acquisition another way is through a secondary transaction of selling I think the secondary transactions are far and few between and very difficult so I wouldn't um Bank on it let's just say um listen you have to be patient that's the reality of it and you know some people say it's a seven to 10 year game but it's really more like a 12 year game so um you know you may have some lucky stuff you know like I was for example you and by the way like a lot of it is imaginary right like so I'll give you an example like I invested I was one of the larger investors in fig AI which is a humanoid robot um yeah and we we funded um last year Brett when no one wanted to do it first of all the market was and so people were afraid and second of all people like didn't believe that he could build a prototype in in a year and so there was a it was a really binary reaction either you thought he was bananas and he would never do it or you thought he was next Elon and he'll he'll do it so I was on the other side of that coin where I thought he could do it and you know that bet paid off for me theoretically now right because Microsoft and open Ai and Nvidia came to lead the next round uh and his progress is astonishing pretty much um I saw that demo uh I don't know if you posted in the group but uh the figure AI demo where it's open AI kind of while m in there while it's the robot's actually doing the uh yeah yeah it's it should it's like yeah it was he posted it yesterday on his Twitter it was insane like it's amazing it talks to you it it's very de dextrous it you know can pick things up it can tell you what what's edible it's it's pretty crazy um it's shockingly crazy uh and so the point of that is is that okay great I got a 6X markup in in a year which is crazy right but that's imaginary so like I could sit there and you know celebrate that uh but you know as a practical matter it's it's not real it's not like I could really you know sell those shares or anything like that so uh as a you know you just have to be really really patient as a as an investor it's not going to happen and you know you have to also have this mental mindset where you're okay with losing a lot a lot a lot of times let's say frequently losing right and so um that is not something that is really ingrained in most people it is counterintuitive to most human nature and it's the reason why you see a lot of the people who are really great investors are on the Spectrum probably because they they don't experience emotion in the same way that we do right and so you know Buffett and all these other guys you know they definitely are on the Spectrum a little bit at least and so it's hard to change yourself to be like that I think that's uh you very well said in terms of just the timing the understanding of failures and just and also just the fact that it is 12 years like you know all these Venture funds are seven to 10 year time Horizons and if you're early stage it's just like you know who's who's exiting and you know that quickly at least an entire fund um so I think you you share a good perspective for I think not just for the founders listening and understanding this but also you know the investors that you know tune in um y Shane it's it's been absolutely awesome having you on the show and kind of sharing these I had a lot of fun thank you for having appreciate this is this is a good dialogue and I think it's Unique being able to have kind of exited founder turned investor and kind of sharing the perspective and the mindset that you have and thep deals that you do um what's the best way for for our listeners to to learn more about you and uh you potentially connect with you so for me uh my website I have a contact page uh that that works really well uh or LinkedIn those those are the two ways um that I really get contacted the most and I check those and I respond there so um that's the easiest way for sure make sure to put those in the show notes and then just a fun way to end you know what would be one piece of advice to to Founders that are chasing Angel Capital right now um the one piece of advice is um just be as persistent as you can the minute that you feel like you're going to quit don't do it because that next one will will likely be the one that hits for you that's really it um persistence is the game uh in no matter how distraught you are and how dejected you are it may take longer but it'll eventually happen I think for most people I that's always that's always the challenge it's like keep at it keep keep going even you know then it's like you know what point does it actually you know punch through and and it's it's I mean I mean you know it's easy to say but like obviously if your idea is complete you shouldn't do it right but but if you if you truly believe that that's GNA be good then you should you should pursue it and it and it it could take a really long time yeah that's a good way to say like I think to summarize if if you have doubt as the founder everyone else will have doubt so you have to be a full believer in what you're doing I agree I agree thank you so much no it's was my pleasure Shane it was great having you on the show and uh you know look forward to staying connected yeah me too thanks so much thanks for listening to the show today we hope you learned something valuable and if you did be sure to let us know in the comments or by hitting that like button and if you're a Founder looking to raise Capital then join us at thunder. 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