How Dan Reich Went From Selling Bouncy Balls To 2 Salesforce Exits!
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Multi-Exit Founder Tells All From Early E-commerce Venture to Tech and Beauty
We're privileged to have Dan Reich join us in this episode - a seasoned entrepreneur and investor with an impressive track record of not one but two Salesforce exits! From his humble beginnings selling bouncy balls out of his backpack in high school, he's gone on to found and exit companies in sectors including technology and beauty.
In our conversation, Dan talks about the intricacies of startups, fundraising strategies, and the art of pivoting. He shares candid reflections on his experiences with ventures like Spinback, Tula Skincare, and Troops.ai, each representing different industries and fundraising approaches. It's a great listen for any founder!
Here's what you're in for:
ABOUT DAN REICH
Dan Reich is a serial entrepreneur and investor with a track record of building and exiting successful companies across the tech and beauty industries. His notable ventures include TULA Skincare (acquired by Procter & Gamble), Troops.ai (acquired by Salesforce), and Spinback (acquired by Buddy Media, later Salesforce). Dan's entrepreneurial journey, which began in his teens, has earned him a rep as one of the "coolest people in New York tech" by Business Insider.
Beyond his business acumen, Dan is an active angel investor, advisor, and philanthropist. When not building companies, Dan can be found at New York Giants games, on the golf course, or volunteering for rescue operations at Mount Snow, Vermont. His life philosophy is simple: "I am, and will forever be, a student."
Connect with Dan Reich on:
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Let's Connect:
Guest: Dan Reich â serial founder and investor with exits via Buddy Media â Salesforce and Troops.ai â Salesforce; co-founder of TULA Skincare (acquired by P&G) and DIBS Beauty.
In high school he sold wholesale bouncy balls at retail to classmates, then partnered with a wholesaler to sell urban apparel onlineâan early eâcommerce lesson that led to his core principle: choose business partners wisely.
Spinback measured Facebook ROI for retailers. A strategic fit with Buddy Mediaâs publishing tools created a 1+1>3 merger; ~13 months later Buddy Media was acquired by Salesforce, delivering Spinbackâs exit.
QVC sought digital-first brand launches with âinfinite shelf space.â Dan partnered with beauty experts to found TULA, financed it conservatively for profitability, and scaled through QVC, DTC, and retailâlater selling to P&G.
Troops.ai brought CRM workflows into messagingââtalk to your CRM.â The team went allâin on Slackâs platform early; after Salesforce acquired Slack, Troops was acquired by Salesforce/Slack to accelerate the integration.
Approximate figures mentioned: Spinback (few hundred thousand), TULA (>$10M), Troops.ai (~$23â24M), plus additional rounds for other ventures and funds.
Raise to hit milestones, not for vanity valuations. Avoid the âzombie SaaSâ middle. Cultivate genuine, nonâtransactional relationships (e.g., First Round). âIf you want money, ask for advice.â Personalize outreach.
Jason Kirby: Hey everyone, welcome back to fundraising demystify. Today we have Dan Reich, serial founder, exited founder, and investor joining us on the show today. Dan, welcome to the show.
Dan Reich: Hey Jason, good to be here. Thanks for having me.
Jason Kirby: I'm excited to have you. You have an impressive story of multiple ventures, multiple exits, raising across over a decade of experience. Can you just give the audience a little bit of background on your first entrepreneurial effort and what that's evolved to over the last 15, 20 years?
Dan Reich: Yeah, certainly. For me, it all started in high school. That's really when I started my first company. What happened was I got really into the internet and technology, tinkering with AOL and all of the things from that period of time. And this company called eBay popped up. So I went down a rabbit hole trying to figure out what I could buy and sell. I ended up buying bouncy balls wholesale off of eBay and I would bring them to school and sell them at retail to my friends and people I didn't even know. Big bouncy balls were 50 cents, little ones were quarters, and I made a good amount of money. I was selling them out of my backpack and locker. Eventually I made a good amount of money for a kid in high school, got tired of doing it, gave them all away, created massive chaos in the hallways with bouncy balls flying everywhereâended up getting suspended for thatâbut that was my first foray into hustling, for lack of a better word.
Dan Reich: A friend of mine saw this and said, well, Dan, you know this thing called the internet pretty wellâwhat we now call eâcommerce in particular. He said, my dad knows a guy that has urban apparel he sells wholesale. Maybe we meet with him and maybe there's a world in which you can do what you did with bouncy balls, sell them, but we use him as a partner to get the product. I said, sure. Let's take a trip to meet him at the Jersey Shoreâwhich is foreshadowing where the story ends. We hop in my car, drive down, and get into this warehouse. Folding tables everywhere with clothing: Rocawear jeans, Apple Bottom, Sean John, etc. He says, look, I've got all this product. I know how to do fulfillment and drop shipping, but I don't know the internet thingâand you do. Why don't you build a website, handle sales and marketing, and I'll handle the rest. Great. So we create a partnership. I built the website. I set up a computer and a credit card processing machine at my house. I hired a customer service repâby which I mean my mom.
Dan Reich: I'd get up at six in the morning, run Yahoo and Google ads, go to school. While I was at school, my mom handled orders and customer service. I'd come home and reconcile orders and ads. Rinse and repeat. It was going really well until we started getting a bunch of customer complaints and issues. After enough of them, I went back down to meet my partnerââwhat is going on?â He reassured me it was circumstantial and would be better. So back to work I went. Play it forward a little more: the complaints kept coming in, to the point I got a very specific threatâessentially âdo right by us, we know where you live,â with specific details. At that point I shut the business down. We lost around $2,000 my parents had invested.
Dan Reich: A few months later, my father comes home with a local newspaper: âlook at page six.â I open it and thereâs my partner in a giant photograph getting arrested by the FBI for grand theftâstealing goods off the back of trucks, like The Sopranos. That was my first lesson in business. Two key takeaways: first, building businesses is incredibly funâaddicting. Second, the most important business lesson is to choose your partners wisely. I was fortunate to learn that early. Every business since then I optimize for partners, coâfounders, colleagues. Get that equation right and you're set up for success and also to avoid failureâyou also optimize for fun and avoid misery at work.
Dan Reich: Fast forward: I graduate high school and study electrical and computer engineering in college. I joined a frat. Our frat got kicked off campus after a huge Halloween party. Collegeâme was super sad with nowhere to go on weekends. I went to a local restaurant that let 18+ in, whereas most venues were 21+. I said, I'd love to throw a party here. We'll sell tickets and donate proceeds to the Red Cross. He agreed. We threw the party, it was a huge hit. The next day: âWhen's the next one?â I talked with my engineering friend: âWe should do more and turn it into a companyâand my fatherâs an attorney; he can help the legal stuff.â Game on. We started Runaway Productions: started as a party company and evolved into an events and marketing company. We'd throw parties and bring in local and national advertisers to pay for the events and promote their brands to the college demographic. We did a handful at our college and othersâwe franchised it. It was a ton of fun.
Dan Reich: Every year I'd go to CES with my bossâI was building computers in high school. I stumbled into a booth making speakers and headphonesâcrazy cool. The founder said, âDan, work for me.â I said I couldn't drop out, but Iâd love to work together. I said, âI have this events companyâsend me product and I'll promote it and give it away at a party.â He said, âWe haven't done that. What else?â I asked for a banner to hang behind the artists. He agreed. I get a box of headphones and a bannerâwe throw a huge party. That was the first live event Skullcandy had ever done. Years later at a big concert I saw huge Skullcandy bannersâI remember day zero. That was my second company. It got to the point my roommates helping promote events wanted to compete with meâwhich would be awkward in a shared room. I said, become partners: I'll give you half the company; you do the heavy lifting; I'm going to build another company with my engineering friends. We started TheCampusAtlas.comâa student portal with everything in one place: class schedules, professor ratings, drink specials, weather, emailârolled out to ~8 campuses. We started fundraisingâthis was the Facebook era: âwe can be Mark.â Graduation approached. I connected with someone building in online advertisingâhe'd helped build Advertising.com (sold to AOL for $535M) and was building a nextâgen version with othersâone partner was Yahooâs first sales guy. Too intriguing to ignore. I put Campus Atlas on hold and became an intern at Lotame. We grew from ~10 employees to over 100 and from singleâdigit revenue to many tens of millions. I saw a high-growth ventureâbacked company up close. Incredible. Then I wanted to build my own company again.
Dan Reich: I reconnected with two buddies from college and started Spinback. This was the Facebook era. Every brand knew they needed social, but didnât know how, what it meant, or how much money they made. We solved that: we helped online retailers measure how much money they were making from Facebook. We raised a convertible note from friends and familyâembarrassingly little; effectively bootstrappedâgot it to the point of raising venture capital. Crazy story: we pitched First Round Capitalâthe firm we wanted. Feedback: âYouâre too young for B2B enterprise sales; you need a real enterprise sales expert (they named someone), and you donât have enterprise customers.â Over the next month or two, we did the things they said we couldnât. We flew that sales expert out, got him excitedâhe even told the investors we didnât need him. We also signed enterprise customers like QVC. And we got another term sheet. We showed up at First Roundâs office: âWe did the things; we have another term sheet; we still want you.â Hours later: âWeâre in.â We signed it.
Dan Reich: In parallel we had partnership conversations with complementary players, particularly Buddy Mediaâthe leading Facebook B2B platform with massive distribution and publishing tools. They didnât have our hardcore ROI analytics. Obvious 1+1=3. But weâd just signed First Roundâs term sheet. Mike Lazerow at Buddy Media said, forget the financingâcome partner with us; weâll lock in value now and add fuel to the rocket ship. We had two term sheets. We locked ourselves in a room for ~two days. We concluded: Facebook would likely go public soon at a massive valuation; the market would ask whoâs the leading B2B platform on Facebookâit would be Buddy Media. Through that lens, Buddy Mediaâs upside looked big. We ripped up First Roundâs term sheet (they were cool about it) and merged with Buddy Media. Thirteen months later, Buddy Media sold to Salesforce for ~\$725M. Amazing ride. Mike and Kass built an incredible company. We were fortunate to be part of it.
Dan Reich: As the deal approached closing, I realized I still hadnât built my company. Staying at Salesforceâa great companyâmight lead to promotions and money, but that scared me more than leaving. I left the day we closed and spent ~a year and a half figuring out what to build next. I thought we had so much white space left with Spinback. I reconnected with many old customersâLâOccitane, Under Armour, QVC and moreâpitched a new software idea. Most were in; QVC was especially excited. They asked my thoughts on a strategic initiative: the world was moving from TV/radio/print to digital; their on-air shelf space is finite, but the internetâs shelf space is infinite, and they hadnât done that before; beauty was the fastest-growing category. âWhat about launching a beauty company as a digitally native launch?â For them: prove a business model. For me: build a brand. I knew digital and their business, but not beauty. I knew someone who did.
Dan Reich: I worked out of Great Oaks Capitalâs office; another person there had started and sold Bobbi Brown Cosmetics. We looped him in. Lunch became several meetings with QVCâs execs. We realized: we had the third-largest retailer saying they must make this successful, and we had the pieces. I shelved software and became a beauty entrepreneur. We started a beauty company (TULA). Unlike tech, itâs CPG; we didnât want venture capital or tech valuationsâwe aimed for profitable growth and financing accordingly. We selfâfinanced; each coâfounder (Ken Landis, Dr. Roshini Raj, and me) put in money for product development; then a bit more; then a bit more. We needed working capitalâphysical products require cash up front. We did a friends-and-family convertible note at an embarrassingly low valuationâthis was risky and I wanted them to get a great deal. We launched with QVC, turned on DTC, it went well, built a team. In a product meeting staring at eight lab samples deciding citrus vs lavender, I thought, âWhat am I doing?â Despite traction, I needed to get back to software. Julia Strauss would become CEO; I stepped back to build software. The business worked; we needed growth capital to roll out to Ulta. L Catterton invested and led growth. That was the last roundâwe built profitably and scaled. At exit, itâs reported we did about \$150M in sales when we sold to Procter & Gamble.
Dan Reich: Then I started Troops.ai with Scott, Greg, and Will. Salespeople build relationships but end up doing data entry in CRM. At the time, six of the top ten most-used apps were messaging. What if you could talk to your CRMâlike texting your momâor like Jarvis from Iron Man for sales? We took a contrarian view on database UX and started on Salesforce, the 800âlb gorilla. We saw another startup building a similar chat product. In a week, they (Slack) announced an open API, eyeâpopping user growth, and an \$80M fund. It looked like Facebook but for the enterprise. We went allâin on Slack. We raised from First Round (finally got to work with them), plus Slack Fund (their first Series A and B checks), and others. We worked with amazing companiesâSlack, Salesforce, Shopify, Spotify, Twilio and more. For most of the journey it felt like chewing glassâconvincing the world to use CRM in a new modality. Then Salesforce bought Slack for nearly \$30B; the tide turned. Shortly after, Troops was acquired by Salesforce and Slack to add fuel and deârisk integration.
Jason Kirby: Good question hereâcoming back to Salesforce after the Buddy Media sale, then selling again: what was that like?
Dan Reich: When it became obvious the SalesforceâSlack deal was happeningâand our posture might shift from âkeep people out of Salesforceâ to âaid the new visionââI reconnected with former colleagues from Buddy Media, especially Patrick Stokes (then running platform at Salesforce). We discussed partnership scenariosâthis was publicly a priority. After Slackâs direct listing (we were invited to the NYSEâamazing), Stuart Butterfield often mentioned Troops in earnings calls as exhibit A for Slackâs platform powering missionâcritical processes beyond dev/IT into revenue teams. Both Salesforce and Slack knew we could play a role. Partnership talks evolved naturally into âletâs do this together.â By then, Slack was an investor and customer; we powered their global revenue team for four years. Salesforce was also a customer and channel partner. The acquisition was a natural progression, not a cold start.
Jason Kirby: And postâexitâyour tenure at Salesforce thereafter?
Dan Reich: It was incredibly validatingâpeople thought we were crazy for years, then the SalesforceâSlack deal proved the thesis. I wanted to roll up my sleeves with Salesforce and Slack leadership, but there was massive change; key leaders at both companies left. Opportunities presented to me were bigger in title but less fulfilling than the Troops mission. I made it clear I didnât want a bigger roleâjust to focus on product. They did layoffs; I was includedâamicable and honestly thankful. I canât sit on my hands; I love building. I had already funded and incubated another beauty company (DIBS Beauty, with L Catterton as investor). Now Iâm trying to build and start more companies with amazing peopleâacting like turbo fuel to the coâfounder/CEO.
Jason Kirby: Thatâs an incredible journeyâfrom bouncy balls to SaaS and CPG exits. Since the show focuses on fundraising: across the businesses you've built, how much have you raised in aggregate?
Dan Reich: Spinback: a few hundreds of thousands before exiting to Buddy Media. TULA: north of \$10M. Troops.ai: about \$23â24M. DIBS Beautyâconfidential, but L Catterton invested. Iâm launching another beauty company this year with a seed round of a few million. For companies where I wasnât the primary operator: Buddy Media raised on the order of \$100M; Lotame had raised \$30â40M around that time. Iâve seen and lived the fundraising arc.
Dan Reich: What many founders get wrongâmyself included at timesâis thinking fundraising is the end game. Raising a lot at a big valuation becomes the celebration, justified by X months of runway. Wrong framework. You raise to hit specific milestones that require outside capital. Historically: preâseed (idea â something tangible), seed (get into market), Series A (prove repeatable scaling to a finite group), B (scale), C (scale toward IPO), then maybe IPO or further. Those are milestoneâdriven raises. When money was free, people optimized for dilution and vanity. The goal is not big rounds or valuations; itâs building a profitable company you can sellâprivately or publicly. If you take outside capital, you must return it with gainsâthere are only a few ways to do that. You need a clean incentive structure so you and your investors can honestly decide when to sell or keep going. Getting ahead of your skis creates broken incentives and makes hiring and exits hard.
Dan Reich: Today I see two interesting camps in software: (1) teams that can go far with little capitalâbootstrap/light seed to profitability (Iâm an investor in some; their updates start with âweâre profitableâ). (2) Deep tech that justifiably needs a lot of capital (semiconductors, fiber, humanoid robots, cars, genetics). Then thereâs a middle bucket thatâs easy to get wrong: raise a bunch for SaaS, spawn 30 copycats funded by other VCs, race to the bottom on price and featuresâhello zombie SaaS. Itâs better to learn fast whether youâll win or die, then move on, rather than float in between.
Jason Kirby: I wish founders would take advice sooner. Many keep going when signs are clear they should probably give up.
Dan Reich: Itâs tough. Sometimes the signs also point the other way. Chris Fralic at First Round would remind me: Roblox was flat for ~8 years, then went parabolic. At Troops we felt that at times; we had clear indicatorsânet dollar retention/expansion, customer feedbackâthat this was the future. Timing matters. But broadly, too many founders optimize for the wrong things in financing and forget first principles of building a successful business.
Jason Kirby: Venture is sexyâvalidation and big paper valuations; thatâs a false North Star. The best capital often chases the better built, profitable businesses. On First Roundâyou said no, then yes, then no, then worked with them later. How do you manage those relationships so money is there when youâre ready?
Dan Reich: The companies that worked did so because of great relationships across the teamâinvestors included. With First Round, Chris is a good friend and great humanâsomeone you want to keep in touch with regardless of deals. You canât do that with everyone, but you keep a handful of great people in your life; some become point guards to your forwardâinvestors to founders. If youâve had a win together (e.g., TULA with L Catterton), theyâll want to work with you again.
Jason Kirby: Important to keep relationships vibrant for more than just asking for money. Youâve also investedâwhatâs it like on the other side, as an angel or LP?
Dan Reich: I remember wishing and praying for a yes when raising moneyâand usually hearing no. Itâs exciting to give back and be the yes sometimes, to help founders chase their dream. Angel investing is less about money (these are lottery tickets) and more about staying part of the ecosystem and helping new startups lay a foundation to win.
Jason Kirby: If founders listening want to approach you as an advisor or investor, how should they do it?
Dan Reich: If you want money, ask for advice; if you want advice, ask for money. Itâs about avoiding overly transactional dynamicsâyou donât want a bad marriage. Ask for advice so both sides can âdateâ and see if thereâs mutual value. With me, I love hyperâpersonalized, thoughtful outreach with an interesting discussion. Thatâs how I know if I can bring unfair advantagesânot just a check. Otherwise Iâd keep money in public markets. Be personal in outreachânot just to me, to anyone. You can find me on social as @danreich.
Jason Kirby: Weâll put links in the show notes. If you acknowledge me rather than AIâskim my LinkedIn, youâll likely get a responseâeven if itâs a no. Broad, copyâpasted asks are easy to ignore.
Dan Reich: I still get emails asking to invest in Troopsâafter the acquisition. Do your homework. Be thoughtful, engaging, and deliberate. It makes a huge difference.
Jason Kirby: Dan, this has been greatâinsightful stories and a unique, successful journey across multiple avenues. Appreciate you being on the show and sharing with our audience.
Dan Reich: Thanks Jason. Thanks for having me.