Founder @ Cakewalk | Making big-company employee benefits easy and accessible for SMBs. Practical lessons from the frontlines of building an insurtech startup.

Hoboken, NJ
1/ Today is Cakewalkโ€™s 2 year incorporation anniversary. Weโ€™ve been live for 18 months and helped thousands of small businesses. The reason we started this still feels the same.Small business owners want to offer great benefits. They just donโ€™t want to become benefits experts or deal with all the broker and carrier complexity. ๐Ÿงต
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ืžืฉืคื—ืชื™ ื•ืื ื™ ืžื•ื“ื™ื ืœื›ืœ ืžื™ ืฉืžืชืคืœืœ ืขื‘ื•ืจื ื• ื•ืชื•ืžืš ื‘ื ื• ื‘ืชืงื•ืคื” ื–ื•. ื—ื™ื™ื• ืฉืœ ื ืจื™ื” ืขื“ื™ื™ืŸ ืชืœื•ื™ื™ื ืขืœ ื‘ืœื™ืžื”, ืืš ืจืื™ื ื• ื›ืžื” ืกื™ืžื ื™ื ืžืขื•ื“ื“ื™ื ื•ืื ื• ื ืื—ื–ื™ื ื‘ื”ื ื‘ืชืงื•ื•ื”. ืื ื• ืžืืžื™ื ื™ื ื‘ื›ื•ื—ื” ืฉืœ ืชืคื™ืœื”, ื‘ื›ืš ืฉื”' ืฉื•ืžืข ืชืคื™ืœื•ืช ื•ื™ื›ื•ืœ ืœืจืคื ื’ื ื›ืืฉืจ ื”ืจื™ืคื•ื™ ื ืจืื” ื‘ืœืชื™ ืืคืฉืจื™. ืœืฆื“ ืชื—ื•ืฉืช ื”ืชื•ื“ื” ื”ืขืžื•ืงื” ืฉืœื™ ืœื›ืœ ืžื™ ืฉื“ื•ืื’, ืื ื™ ืžื‘ืงืฉ ืฉื”ืชืคื™ืœื•ืช ืขื‘ื•ืจ ื ืจื™ื” ื™ื›ืœืœื• ื’ื ืื™ื—ื•ืœื™ื ืœืจืคื•ืื” ืฉืœืžื” ืœื›ืœ ืžื™ ืฉื ืคืฆืข ื‘ืื•ืจื— ืงืฉื” ืžื™ื“ื™ ืžื—ื‘ืœื™ื. ื ืจื™ื” ื•ื—ื‘ืจื™ื• ื”ื ื”ื’ื™ื‘ื•ืจื™ื ืฉืžื‘ื˜ื™ื—ื™ื ืฉื ื•ื›ืœ ืœื”ืชืžื™ื“ ื•ืœื ืฆื— ื‘ืžืื‘ืง ื ื’ื“ ืืœื” ืฉื–ื•ืจืขื™ื ืจืฆื— ื•ื”ืจืก. ื–ื”ื• ืžืื‘ืง ืขืœ ืขืชื™ื“ ื”ืฆื™ื•ื•ื™ืœื™ื–ืฆื™ื”, ืœื ืคื—ื•ืช.
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how weird do @sama and @DarioAmodei have to be to make @finkd look like the rock star cool kid on the block?
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Really cool opportunity with a great company for my TLV network.
The Information is hiring our first Israel Bureau Chief as we ramp up our international expansion! Ten years ago, we opened an Asia bureau and cemented a leading position in covering China tech. Last month, we welcomed our first reporter in Singapore. And as I searched for our next hub, I was looking for a place whose tech industry is woefully under covered relative to its significance, and the answer was clear. Israel is at the center of three of the most important tech trends of the day: AI, cyber and defense. I can't wait to build this team together with an awesome bureau chief. Check out the role here. ats.rippling.com/theinformatโ€ฆ
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Jonathan Morav retweeted
The Information is hiring our first Israel Bureau Chief as we ramp up our international expansion! Ten years ago, we opened an Asia bureau and cemented a leading position in covering China tech. Last month, we welcomed our first reporter in Singapore. And as I searched for our next hub, I was looking for a place whose tech industry is woefully under covered relative to its significance, and the answer was clear. Israel is at the center of three of the most important tech trends of the day: AI, cyber and defense. I can't wait to build this team together with an awesome bureau chief. Check out the role here. ats.rippling.com/theinformatโ€ฆ
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unpopular take: @Muse is running laps around @bot
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Jonathan Morav retweeted
Today I met Marc @Benioff, founder of @Salesforce. I asked if he wrapped Tefillin. โ€œOf course. Whatโ€™s the question?โ€ He told me heโ€™s been wrapping consistently for 30 years, every morning, and that itโ€™s become a meditation that brings tremendous blessings into his life. Heโ€™s been doing it since before he even founded Salesforce. Marc thanked me for the work Iโ€™m doing with Tefillin and emphasized how important it is. It was also inspiring hearing about his legendary 1-1-1 model: 1% of equity 1% of product 1% of employeesโ€™ time Dedicated to giving back. That model has since been adopted by 20,000+ companies. A true example of building a company while building a culture of giving. Truly inspiring.
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36 hours into Omarchy on my old dusted off M2 Pro. Did I say I am never going back? @dhh @OmarchyMac @OmarchyLinux
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I am 24hrs in to @OmarchyLinux on my M2 Pro MacBook. I dusted it off (I have M4 Pro Max MacBook and M3 Ultra Mac Studio at the office). How can I ever go back to MacOS? Thank you @dhh @OmarchyMac
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converted an old macbook pro m2 pro to omarchy os - wow, addicted.
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Jonathan Morav retweeted
.@edsheeran I brought my wife and two daughters to MetLife Friday because we are huge fans of yours. We arrived early, I spent $180 on two sweatshirts for them, watched the first two opening acts and were having a great time. Then Macklemore decided to turn your concert into his political rally. When he started chanting โ€œFree Palestineโ€ and pushing his clearly uneducated version of the Israel/Gaza conflict, my daughters looked at me completely confused. I had brought them to an Ed Sheeran concert, not to have an opening act lecture them about Middle East politics. After Friday night, I started looking into Macklemoreโ€™s history. What I found, including his repeated use of antisemitic tropes, made the whole thing even worse. So I took my family and walked inside alongside hundreds of your other fans. As we were walking in, even the MetLife security guards were rolling their eyes at what was happening on stage. We waited until Macklemore was finished before returning to our seats. Then we watched your show, which was phenomenal. I left Friday hoping maybe this had caught you and your team off guard. Then tonight you allowed it to happen again. You knew exactly what Macklemore had done the night before, and you gave him the stage again. Friday might have been Macklemoreโ€™s decision. Saturday was yours. You have a lot of Jewish fans who love your music, buy your albums and merchandise, and bring their kids to your concerts. Tonight, you lost four of them. And I suspect plenty more. @CombatASemitism @StopAntisemites
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40 handoffs. 8 to 12 weeks. cakewalk does this in minutes because a 10 person shop does not have a benefits department and we built for that on purpose. 1200 businesses in. the next 1200 get the same promise. great benefits. no expert required.
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80% of workers take benefits over the same job plus 30% more cash and nothing. aicpa / harris. a small company should be able to offer that. most still cant without the owner taking on a second job. that is the gap.
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know your metrics cold. chase truth, not hype. i want cakewalk to be the number one digital benefits platform for small businesses in america. bar none. that only happens if the numbers are real and the customers are real.
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founders two years in. which one actually bit you. wrong cofounder. didnt know the customer. built too slow. the mission does not care which one it was. you still have to face it.
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fragmentation priced small business out of great benefits. brokers, gas, carriers, tpas. every layer takes a cut. none own the outcome. cakewalk exists to collapse that into one promise. choose, launch, manage. price them back in.
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almost 40% of people who go to work in this country work at a company with 50 people or less. they deserve the same quality benefits a fortune 500 employee gets. the stack treats them like an exception. they are the market.
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"we need proof in 30 days" used to piss me off. it is a gift. it kills the six month fantasy. what is left is the smallest thing a real customer will touch. the mission does not need the fantasy.
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a 12 person company ghosts the broker after meeting one. not because they dont care. they could not see the next step so they picked none. that is the floor of this market. served badly or not served at all.
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can cakewalk save you money on healthcare today? no. not until we have more scale. i say that on calls. the mission is not a cheaper slide. it is taking the second job off the owner so they can offer enterprise grade benefits without becoming an expert.
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if you run 5 to 25 people and you last tried to put benefits in place, what actually stopped you. price. time. or it felt like a timeshare. none should not be the default. owners care. the system made caring a second job.
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