Full Transcript

Jason Kirby: Hello everyone, welcome back to Fundraising Demystified. Today we have Shane Newman with us today. Welcome to the show, Shane.

Shane Neman: Thanks so much. Thanks for having me, Jason. Appreciate it.

Jason Kirby: Now I'm excited to have you. You have an extensive entrepreneurial background, launching your company in the early 2000s—kind of before it was cool to do a tech startup, after the dot‑com era. Then into the mid‑2010s, selling your companies, gaining extensive experience, and having that opportunity as an exited founder. It'd be great for you to share your background, how you got started as an entrepreneur, and where you are now.

Shane Neman: Sure. My entrepreneurial background was pretty unlikely, just to be honest. Well, listen, I guess it is unlikely and likely at the same time. My parents were immigrants that came here with nothing. They were entrepreneurs and I watched them live the American dream. They came with nothing.

Shane Neman: They worked really hard, started small businesses, built themselves up, worked pretty much 24 hours a day, and had the hustle—let's just put it that way. I watched them do that growing up and better our lives over time. When it came time for me, I ended up after college going to medical school.

Shane Neman: That was the path I thought I'd go down—becoming a doctor. I did pre‑med 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. I worked during college as a programmer, so I ended up making a good amount of money and getting a taste for what it entails and how it feels. Especially at that time, knowing web programming in the late 1990s, I was getting paid what a lawyer would get paid per hour.

Shane Neman: I had a college roommate, a friend from high school, working at Goldman. I was in medical school. He was partying, having a good time, and I was watching him make a lot of money. He came to me on a Sunday while I was studying and said, “What are you doing? We can make millions of dollars. I can raise all the money and you can create software, and I have an idea.” That was it. I quit that day.

Shane Neman: 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 during the dot‑com boom. We created a company called Offix, essentially Microsoft 365 delivered via Citrix. It was a web portal that businesses could use to log in and give apps to their employees—Microsoft Suite, QuickBooks—anything Windows‑based. We had an app store, we hosted your files in the cloud; we were a SaaS business—but none of those words existed.

Shane Neman: We didn't even know how to describe it properly, and people didn't know how to consume it because they weren't used to paying monthly or yearly for software. They were used to buying software and then upgrading. Suffice to say, that didn't work out. After two years, the dot‑com bust happened. I left with nothing. I was pretty broke at that point. I moved in with my girlfriend at the time; she was going to FIT. She lived in a dorm and I lived with her to save money.

Shane Neman: She would work at a few nightclubs on off nights to make money. I would go with her because nobody needed programmers then—dot‑coms had gone bust. If you can believe it, programmers couldn't get any love at all. Now you don't let go of the best ones; they're impossible to find.

Shane Neman: I started looking around me. Everything was antiquated in the nightclub business. To shorten it, I created a company called Joonbug—really in her dorm room—bootstrapped and scrappy, but it became the de facto tech stack for nightclubs. We created ticketing, marketing, the system they would run their clubs on. We also had a consumer‑facing site where we built a million‑person email list of people who go to events and we monetized that database. So we had the SaaS business, and we also did events ourselves—eating our own dog food.

Shane Neman: I built that business large over eight or nine years. We had about 100+ employees, doing high tens of millions in revenue. Around 2005 I realized email efficacy was dwindling—everybody had MailChimp or Constant Contact. Now you're getting emails from Joonbug, the promoter, the DJ, the venue—their grandmother—everyone.

Shane Neman: I wanted to cut through the clutter. BlackBerrys had come out and texting was becoming prevalent. We needed to send text messages to everybody. There was no off‑the‑shelf solution—Twilio didn't exist for another four years. As far as I know, we became the first publicly facing SMS API in the U.S. after I built that, but we focused on a MailChimp model: a business would pay monthly, run campaigns through us, manage contacts, get widgets—the whole ESP‑style playbook.

Shane Neman: I ran the two businesses side by side for about a year, then sold the nightclub software business and focused on Easy Texting—put a lot of that money into it. I ran it another eight years and grew it to a little over $15M ARR, then sold in 2013 to a strategic who raised money through Morgan Stanley and Investor Growth Capital. I stayed a bit over a year, moved to Miami, and for the last decade I've been learning to run my own family office—real estate, private equity.

Shane Neman: My passion is early‑stage venture. I spend most of my time there, working with founders in all kinds of businesses: biotech, food tech, CPG, crypto—anything opportunistic that makes sense.

Jason Kirby: You have such a fascinating story. I want to unpack a few pieces—being on the bleeding edge. In 1999, “the cloud” wasn't a word. Selling that through taphors must have been a nightmare—hence why it probably didn’t work out, even though it was the future. Then recognizing the vertical SaaS opportunity for nightclubs and building EZ Texting to solve your own problem—and retaining that business after selling Joombug. Smart deals and innovation that put you in an enviable position.

Shane Neman: The grass may seem greener, but the grind never leaves. But yeah, listen, it doesn't suck. I won't bullshit you.

Jason Kirby: That's 16 years of grinding—building a company that failed, then one that succeeded, selling it, and continuing to build—until you earned your seat to be more comfortable and choose what you grind on.

Shane Neman: Yes, that's true. The one thing I get to choose is how I spend my time—that's the most important thing. But I do choose to work a lot still. That's either in you or it's not. There's no replacing hard work—this is all cliché stuff anyway.

Jason Kirby: Speaking of books, you have Nightlife Lessons. Tell the audience what's in it.

Shane Neman: I have it right here. The book came from reiterating the same stories to founders I work with. The most interesting stories came from Joonbug—I got screwed every which way in that business because of the people and industry. I learned what to do and not to do, how to read customer psychology, and anticipate 10 steps ahead. Each chapter is a lesson, and winds down with how I applied it later at Easy Texting or now in venture. It took two years to write—labor of love. Not enough people will read it to be profitable, but if it helps a few, great. I've got 60+ five‑star reviews—which is funny because I don't even have 60 friends.

Jason Kirby: This show is a lot about fundraising and capital. What were some of your struggles there?

Shane Neman: I bootstrapped the last two businesses mainly because I didn't want to go the VC route after a really bad first experience. We raised from friends and family who didn't remain friends and family after we lost their money. If you're willing to lose those relationships, sure—but money changes how people interact. Also, we might have survived if VCs had continued funding what they committed—but they didn't. I was jaded. As a bootstrapped company you act differently—more careful and cautious. Maybe you don't grow as fast; pros and cons.

Shane Neman: I'm a VC now, so I want people to take my money. But VCs want to invest in businesses that don't need the money. Founders should aim to be in that position—the business is so good you don't need the VC, and the VCs want you.

Jason Kirby: Many early founders talk about the chicken‑and‑egg problem: “I can't build it without money.” Thoughts?

Shane Neman: Today you can build almost anything without money—or very little. Not an excuse. Tools are free or have credits. No‑code/low‑code exists. Even patents—I've backed a founder who convinced a top law firm to file for free because the idea was strong; he’d pay later. There's always a way if you're willing to learn and grind, or find novel paths.

Jason Kirby: I'm in the camp that you should get something off the ground yourself and ideally get to some revenue before asking for money—back to business fundamentals.

Shane Neman: I agree. Do it as a side hustle if you're employed. Even getting a Shopify store live is easy now—AI can help write your copy. There’s no excuse anymore.

Jason Kirby: Lower barriers also mean more competition; you must differentiate and prove you can sell. Looking at your portfolio: what's your approach to early‑stage investing?

Shane Neman: Some of it is cliché: invest in the founder, not the product—but the product matters too. I don't have a formal process like a VC firm. I answer only to myself, with a longer time horizon. I look for game‑changing things. There are a million "AI wrappers"—being a wrapper around ChatGPT won’t work. You need an edge. It must be category‑changing—or change one critical part of an existing industry.

Shane Neman: Example: I seeded Alermi last year. The founder, Shani, had a DTC nasal spray idea—her dad is an allergist who compounded custom sprays. She knew me from Apostrophe (derm). Initially I passed as too early—no revenue, no data. She came back a year later with $30–40K ARR and amazing reviews. We realized we had something. Allergy space is big pharma—Flonase, Afrin—who is she to disrupt? She did, by using four existing prescriptions and formulating titrations based on symptoms—hundreds of formulations. Asynchronous telemedicine with in‑state allergists, free trial, then subscription. They ended the year with ~$4M ARR—from $40K. We funded a $3M seed in Jan last year; now they’re raising an A with big VC interest. She didn’t reinvent the wheel; she made it better. And she listened—coachability matters.

Shane Neman: On the flip side, I was on a call with a founder. I said, “Send me a separate email with a blurb and deck so I can forward to four friends.” The founder replied to the original thread with attachments, then another email with what they forgot. Do they think I'll recompose their email? Simple stuff like this reveals a lot. I knew I couldn't do anything with that founder. Know your numbers; don't make them up.

Jason Kirby: It’s a relationship game. Founders must make it stupid‑simple to help them. Any deliberate stress‑tests you use with founders?

Shane Neman: I ask questions designed to piss you off and see how you react. A few weeks ago, a founder with two prior failures got combative when I asked why this time is different. I told him: I can be nice or kind. Nice is “thanks, bye” and never responding. Kind is honest feedback: your presentation sucks, your attitude sucks, go back to the drawing board, keep your cool. VCs don't have to deploy. Bedside manner matters—if you want to raise, you have to play the game.

Jason Kirby: What grabs you in a cold or referred email?

Shane Neman: Exactly what you do in one sentence, then stats. I’m human—warm intros help—but I try to read every message from my site and respond, even if it's a no. This is a marketing game—you have two sentences and the subject line to get attention. If you can’t concisely and completely tell me what you do, you don’t know your own business. Skip the “I saw you invested in X so you should invest in us” angle—that can be counter‑productive; I already have exposure.

Jason Kirby: Getting into deals is one thing—what about getting out and generating returns?

Shane Neman: Liquidity can come via acquisition or occasional secondaries. Mostly, be patient. People say 7–10 years, but it’s closer to 12. I had a biotech IPO this year, but lockups mean no immediate liquidity. Markups are often imaginary until realized—e.g., I was an early investor in Figure AI (humanoid robots). We funded when the market was rough and many doubted they could build a prototype in a year. It was binary: either bananas or the next Elon. I believed. It paid off theoretically with a big markup as Microsoft/OpenAI/NVIDIA came in—but again, unrealized until liquidity.

Shane Neman: As an investor you must be okay losing frequently. That’s counter to human nature, which is why many great investors have an unusual emotional profile.

Jason Kirby: Great perspective for founders and investors alike. It's been awesome having you and hearing the mindset and deals you do.

Shane Neman: I had a lot of fun. Thank you for having me.

Jason Kirby: What's the best way for listeners to learn more and connect?

Shane Neman: My website contact page or LinkedIn. I check and respond there—the easiest way.

Jason Kirby: We'll put those in the show notes. Final question: one piece of advice for founders chasing angel capital?

Shane Neman: Be as persistent as you can. The minute you feel like quitting, don't—because the next one might be the one that hits. Persistence is the game. Obviously, if your idea is complete shit, don't do it. But if you truly believe, pursue it—it can take a long time.

Jason Kirby: Well said. If you have doubt as the founder, everyone will have doubt. Thanks for joining, Shane.

Shane Neman: Thank you so much.