18 Dec Republican Lies Cost Me The Election: Insights from a 1st Time Candidate for Office in New York

I lost. But I also won. Here are my reflections and insights about politics, campaigning and the future of our great democracy. (Be warned, this is a lot longer than my usual articles. It’s one part narrative, one part election analysis and one part advice for future first-time candidates for office. Maybe I’ll have to turn it into book #6…)

Over the last nine months I’ve worked nearly 7 days a week, 10-12 hours/day on my first campaign for public office. I’ve always wanted to serve my community- while I only taught for three years, I loved having an impact on my students. And while I’ve been in business for most of my career (7 businesses, 5 books, dozens of keynote speeches around the world), my greatest joys in my career have been in impacting the lives of my employees, mentees, clients, readers and audiences. And my proudest accomplishment in my career was winning Crain’s Best Places to Work in New York five years in a row with two different businesses – “Could I actually one day make government a great place to work?,” I wondered.

My Inspiration To Run for Office

When I met the amazing Senator Frank Lautenberg on a plane 14 years ago, I was inspired by his turn from business (ADP) to government. He became an instant mentor, and I knew I wanted to one day run for office – when the time was right. He insisted I work on my then-new business and family with two young daughters at the time, and along with my wife Carrie, we did just that. We were fortunate to have another child (Seth Franklin!) and grow Likeable to become one of the premier social marketing firms in the world. We sold Likeable and I started a bunch of other companies along the way. Some failed, which is ok, as we learn more from our failures and mistakes than from our successes. I wrote books about the lessons learned from the failures, enjoyed the successes, and bided my time.

This January, I thought the time might be right. My girls were older, with Charlotte in her senior year of college and Kate in her senior year of high school. While Seth was just 10, I thought if I ran for a local position now, I could have a lot of time with him, and perhaps still have time to follow in my mentor’s footsteps in government if things went well. I had little interest in a legislative role, but with significant experience leading and growing businesses as a CEO, I figured an executive office would be a good fit. After a long, soul-searching meeting with Carrie, we decided I would explore running for Town Supervisor of our town of North Hempstead in Long Island, New York.

(Side note: Town Supervisor is a horrible job title, it sounds like a small office manager, not the chief executive of a community of over 240,000 people, larger than Boise, Richmond, Salt Lake City and Des Moines. It’s a pretty big deal, but you’d never know it from the job title!)

I approached two people first: Jon Kaiman, the former Town Supervisor and Democratic Congressional Candidate, and Mariann Dalimonte, our local Town Board Council Member. They both warned me that in this political climate, it would be a tough campaign, and that the Republican party would send negative mailers about me. They had sent over 20 negative mailers targeting Kaiman when he ran for Town Supervisor two years prior.

I wondered: Would they bring up my first night on Paradise Hotel, the reality TV Show I was on way back in 2003, when I had too much to drink on my first night? Or perhaps the many speeding tickets I got when I was a lot younger? Or my love of poker and gambling in general? Or even an antisemitic trope?

Still, I was feeling determined, and with the unwavering support of my wife, took the next step, and met with the Town Democratic leader Sabi Samet and then County and State leader Jay Jacobs. They also said it would be tough, and I would have to raise significant money to compete – but if I were up for it, they would support me, effectively meaning I wouldn’t be primaried and I would face off against the Republican incumbent Jen Desena on Election Day in November.

If you’re wondering, “Why Democrat?”, allow me to expand for a moment here transparently. I’ve been a Democrat my whole life, always feeling like the social compassion and caring about my fellow humans was best represented by the Dems. It wasn’t always perfect, but it felt like the best fit. As we achieved personal success in business and gained wealth, I became more fiscally conservative- in favor of less government and lower taxes. But I still believed strongly in gun control, women’s reproductive rights, and LGBTQ rights. I was a Democrat!

On October 8th, 2023, my affiliation with the Democratic party was most challenged. The day after the most gruesome, devastating attack on the Jewish people since the Holocaust, there were people – all Democrats-  marching in the streets against my homeland of Israel. I felt angry, disillusioned and abandoned. I even considered switching parties or becoming an Independent. But I didn’t. Those beliefs above, along with my repudiation of MAGA and Trumpism, kept me a Democrat, albeit a Zionist pro-business Democrat.

So after a final meeting with Carrie, I decided officially to throw my hat in the ring and run for Town Supervisor. I would have to form a committee, hire a treasurer, and make an announcement that I was running. Then I’d have to build my team, fundraise, create a campaign strategy, get on the ballot through petitions, campaign all summer and fall, and hopefully win in November against Republican incumbent Jen Desena, who seemed like a nice woman who didn’t have much experience or ability leading. It seemed strange that I was expected to raise over $500,000 to win a $133,000 job, but I assumed I’d have lots of help along the way.

A week later, my poker-buddy group chat lit-up about a pro-Gaza fundraiser that was taking place in our town at a pizzeria. I immediately researched PALI, the organization hosting the event, saw several extremely offensive, antisemitic, hateful social media posts (“Long live the Oct. 7th Martyrs”, for example) and sprung into action.

Along with a handful of other community leaders, we quickly organized a rally protesting the event. 200+ people showed up on a snowy night within 2 hours to “Stand Up Against Hate.” I was not protesting the fact that they were raising money for starving children in Gaza of course, but the organization that sponsored it. Unfortunately, a few protestors spewed hate themselves, calling attendees “terrorists” and other slurs. I immediately chastised those I heard – but the damage was done – ironic for a protest against hate, I know.

When I announced my candidacy a week later in front of 100 friends and supporters, it was exhilarating and exciting. Democratic activists came that I had never met. In the room, we probably had 70 Democrats, 10 Republicans and 20 Independents. But I soon learned that many far left Democrats in town opposed me – some even calling me Islamophobic. This was a shock to my system and heartbreaking really, since they obviously didn’t know what was in my heart.

Even though I would face brutal and relentless attacks from Republicans via people’s mailboxes, the most brutal verbal attacks face to face were from fellow Democrats – who throughout the last 9 months would call me “Islamophobic,” “Jackass”, and “Racist,” amongst other things. It was also the first time I realized how true the adages are: I’ve now heard that “Republicans fall in line, while Democrats fall in love.” And “Republicans are soldiers while Democrats are questioners.”

Some question-ers at least approached me and gave me a chance. Nina Gordon attended my launch after emailing me questioning my decision to lead that rally. Then we talked – and she quickly went from being a skeptic to one of my biggest supporters. She is certainly more left-leaning than I am – but I am proud to call her and her partner Brett, friends, today. I would later meet with Islamic leaders in town including some folks that were at that event – and through an emotional meeting, deeply connect over our shared humanity. I do wish I had done a better job of making other Dems fall in love with me.

The Campaign Takes Off

The next stage in the campaign was getting on the ballot.  Volunteers from the Democratic party worked super hard to get me on the ballot as a Dem, but I wanted a 3rd party line as well. I knew that in red-Long Island, my best chances of winning were distancing myself from the far left – plus I felt much more comfortable in the Middle. After toying with a bunch of more innovative identity-based 3rd party ideas (Am Y’israel Chai, Jewish Asian Voter Alliance), we settled on the Moderate line – I really do believe both parties have gotten too extreme and that most people are in the middle. I hoped the Moderate line would unite people and win over the large Independent voter constituency. But this upset many Democrats – so we were on our own to get the signatures required to get on the ballot.

Who is “We”? This is a good moment to introduce the amazing group of candidates that worked together in our town – Jason Lew was my effective running mate – a Chinese American business person who ran for Town Clerk and would become a great friend throughout the  journey – and Robert, Vivianna, Delia, Lisa, Liza, Juleigh, Paul, Karen, Wayne, Joylette, Seth, and Nicole, along with everyone’s campaign managers and our town Dem leaders. A few days after the election, as I write this, I miss them a lot – it’s like summer camp – we spent so much time together all Summer and Fall long, and now it’s back to business as usual all of a sudden. They are an amazing group of people who inspired me with their courage to run and their incredible work-ethics.

After getting on the ballot in May, my attention turned towards building my team and fundraising. I hired a treasurer and a couple of consultants. Political consultants, I learned, are essentially direct mail vendors. They don’t charge for their consulting but instead make enormous margins on direct mail. Seemed like a necessary if opaque expense, so I went with it. Not surprisingly, they said direct mail was the most important aspect of the campaign. I planned on hiring a campaign manager once I had raised more money.

Political fundraising turned out to be the hardest thing I’ve ever done in my career: Harder than building businesses, writing books or raising venture capital financing! While I’ve gotten lots of experience over my career asking for money, folks always got something in return more tangible: a product or service they bought from me, or equity in my company. What made this so hard is that here, they were only getting the good feeling that they supporting a friend or fellow townsperson. It was super difficult to ask friends who didn’t live in our town to give me money, and hard to ask strangers in our town as well. Eventually, I got better at it, and towards the end, raised about $250,000 total – a lot less than my opponent, who had over $1,000,000 thanks to the Nassau Republican Party, but nothing to sneeze at. I am so grateful to everyone who supported me financially – from those who gave $5 to those who gave $5000!

Late spring and summer, I developed my platform and website, and my weeks were filled with campaign events and appearances. It seemed like every day there was an event to attend somewhere, if not two or three. I met hundreds of new friends all over our town and had so much fun going to events. I’m fortunate enough as an entrepreneur to be able to go to these – but I’m unsure how anyone with a 9-5 job can ever run for office effectively.

As someone whose career began as a dancing, screaming “Crunch n Munch guy” Boston sports vendor, and whose entrepreneurial career kicked off with a sponsored ballpark wedding, and who reached 200 million views when as CEO of a mental health marketplace I offered “Free therapy for Mets fans,” I knew I had to do things the only way I knew how: Out of the box. So I launched a podcast about life as a candidate, made an appearance as Elvis at a Seniors event, threw out the first pitch at a Mets game, and gave away 2,500 Halloween “Safe with Dave” flashlights and 25,000 fortune cookies saying prosperity was on the way if you voted for me. I joyfully sang – twice- at the First Baptist Church in Westbury. Thanks to a talented family friend, we even had a campaign theme song and music video. These things may or may not have helped the campaign, but they sure made it fun for my team and me!

I crushed my opponent at the the one debate she showed up at, but it didn’t matter. I got endorsements and support from the NYPD, Sierra Club, Planned Parenthood, Moms Demand Action, They See Blue, and the Forward Party. But sadly, none of that seemed to make a difference. I was supported by people as far left as Randi Weingarten and as far right as Anthony Scaramucci – but I’m unsure what impact if any that had. Meanwhile, what I strongly believe made the ultimate difference in sinking us (yes, the consultants were right): the 5 truthful mailers I could afford to send out versus the 16 deceitful mailers my opponent sent out!

The Mamdani of North Hempstead?

I will never forget the moment the first mail from my opponent hit mailboxes. I was in LA with my family, moving my daughter Kate into her dorm room at USC. I had just walked 12 duffel bags up 4 flights to her room on a hot August day. I looked down at my phone and saw I had 8 new text messages in the last two minutes. Then I opened up a text with a picture of the first Desena mail:

My face must have turned pale as my wife immediately said, “What’s wrong?!”

“The fist mail just hit,” I replied. “And it’s insane.”

Yes, I had been warned by mentors and consultants about the negative mail. But I can’t imagine anything would have prepared me for the emotional hit of seeing such nasty lies written about me and sent to my entire town in writing. It was so absurd, it would be funny – if if weren’t so cruel and deceitful. It turns out, this mail and the 15 (!) mails that would follow it calling me dangerous, a “criminal’s best friend,” “anti-police,” “another NYC extremist,” and “secretly bankrolling a radical activist group” were “sourced” by a $10 contribution I gave to a friend running for local office on the Working Families Party line in 2011.

Yes, you read that right. It’s hard to imagine this is legal – but defamation is too expensive to fight. Many told me to fight fire with fire and accuse my opponent of supporting school shootings or being on the Epstein list or making up nutty things the way they made up so many things about me. But I refused. I would only fight back with honesty, win or lose.

The onslaught of negative mail continued, with Desena sending out a new mail roughly every three days for the rest of the election cycle. Her strategy was not to mail to Republicans – she already knew they would come out to vote for her, despite the fact that she is ironically a registered Democrat. Instead, she mailed these flyers to Democrats and Independents in the hopes of branding me as an extreme socialist, making them afraid of me, and making them afraid of “Mamdani madness coming to Long Island.” All told, she sent at least 16 deceitful flyers attacking me, and spent at least $1M on the race, while the Nassau Republican party spent roughly $12 million on all of their races, according to Newsday.

The flyers really got to me emotionally. I went to a therapist and my Rabbi for support, but knowing that thousands of people all over my town were getting so much misinformation about me, including my 10 year old son’s friends’ parents – it was very hard to stomach. I fought back in the campaign with a series of “Debunking Desena” videos online, and distanced myself from Mamdani wherever possible. My influencer friend Aliza Licht made a video exposing Desena’s lies and I went on News12 sharing that I consider myself a “Zionist capitalist.” I knocked on thousands of doors, introducing myself to townspeople in the hopes of them seeing the real me.

Election Day Results!

I went into Election Day hopeful and optimistic. I brought my wife and son to the “Democratic HQ Results Party.” My daughter Charlotte even flew in from North Carolina to be there. Friends and supporters came with the hopes that our hard work would pay off. But as the numbers came in, it was clear that the Republican strategy had worked. I got 23,000 votes, which on the one hand is pretty amazing. But Desena got 29,000, beating me 56-44%. Upon a closer look at the numbers it appears likely that she got roughly 20% of the Dem votes and 65% of the Independent votes. They were misled and scared of Mamdani, and voted to keep out this (obviously non-) extremist.

I was devastated. I’ve never worked so hard for anything in my life, and the pain of losing stung. I felt so sad, so guilty for letting down my supporters, so disappointed, and so embarrassed. Those who know me well think of me as the most competitive person they know, and they know I HATE losing. So the pain sucked a lot, and a week later, I’m definitely still grieving.

I’m not sure what I could have done to materially change the results. I certainly could have fundraised more earlier, or hired a campaign manager earlier. That may or may not have made a difference. I could have run a more traditional campaign focused on direct mail only. That would have been boring but might have earned me a percentage point or two. I could have run a more negative, deceitful campaign. Then again, I might have lost doing that and then I’d have to live with myself. I had to be me.

What Can You Learn from My Experience?

I mentioned earlier that we learn more from our failures than our successes, and this experience is no different. I hope these insights prove valuable for anyone out there thinking of running for office, or really anyone contemplating a new venture. Here are my 7 key lessons from the campaign, and how, in a way, I won:

1) Hire for Hustle

I’ve made some poor hires throughout my career, and, unfortunately, this campaign was no different. I’ve written before about the importance of “Hire Slow, Fire Fast” so this time I’ll share that I did make one of the best hires of my career as well: I brought on a totally inexperienced young man late in the campaign to be my campaign manager, and of the 1,500+ people I’ve hired over the years, Erik Simon was perhaps the hardest-working person ever. Working 7 days a week, he was up until 3 am most nights hanging signs and then back at with me fundraising at 9am the next morning. There’s simply no replacement for hustle.

2) Know What You’re Willing to Sacrifice Ahead of Time in Each Category: Time, Energy, Money, Values

I planned ahead and knew I was willing to sacrifice time (lots of Daddy-son and couples time) but not all of it- I’m proud that I didn’t miss a single one of my son’s baseball games, and I still managed to go on many of my weekly date nights. I did sacrifice a lot of energy, but thank goodness for Dunkin’ Donuts and my caffeine addiction. My wife and I agreed ahead of time to invest a substantial 6 figure sum into the campaign, and then resisted the temptation to put more money in late in the game. And most important, I refused to sacrifice my values, and ran a campaign that, at every turn, I could be proud of to my children.

There’s no right answer when it comes to how much time, energy, money or values to sacrifice if you’re running for office or doing any new venture. But the key is committing ahead of time, and sticking to it.

3) Money Matters

Before this campaign, I had no idea how important money was to local political campaigns, or how brutal fundraising would be. But it matters a lot, and a big part of the reason I lost is that we were outspent at least 4-1 and perhaps as much as 10-1. My opponent’s money bought her 16 attack mailers that successfully shaped voters opinion of me. In order to successfully run for office, (or do any new venture) you’ve got to have a plan to fundraise significant dollars.

4) Timing Matters Too!

I thought the timing was right for my family and me. Perhaps it was. I thought the timing was run to run as a Democrat. (Given the national performance of Democrats on Election Day), Perhaps it was. But the timing was not right to run as a Democrat on Red Long Island, just outside of Mamdani’s NYC. It is vital to understand the impact of the timing of your decision to run (or start any new venture).

5) There are Always Many Things You Can’t Control

I couldn’t control the macro climate of Trump and Mamdani. I couldn’t control my opponent not showing up to a debate, or Dems who chose not to support me, or my financial limitations. I’ve written a lot about the Serenity Prayer and the key to life being understanding what we can and can’t control. I could control my effort and my attitude, and my integrity, and I gave 100% each day along those lines.

It’s valuable not to dwell on things outside of our control, but to focus instead on what we can do to make a difference!

6) Relationships Matter Most

My number one lesson is that it’s the relationships that matter most, in a political campaign, in any new venture, and in life.

My relationship with my wife Carrie is stronger than ever, thanks to the campaign, and our reactions to the stress and challenges of it. I lost a couple of friends during the campaign, as I feared I would – people who didn’t feel comfortable crossing party lines to support me – but I strengthened numerous friendships, and made dozens of new friends I hope to keep for life! I met amazing mentors who helped guide me through this journey and who I hope to stay close with and pay back (or more likely forward). I met incredible Democratic volunteers and club members and leaders all looking to change our community for the better. And of course, 600 donors and 23,000 voters picked me, including 68% of my Port Washington hometown – and these are people I will forever be grateful to. The campaign lasted nine months – but relationships are forever.

7. Gratitude is (Always) the Key

Many people think success will bring them happiness and then they can be grateful. My thinking is the opposite: My daily gratitude practices make me happier – and in turn allow me to become more successful. In this election, I was not successful – but throughout the entire journey, at times painful and at other times joyful, I was grateful. And today, I am so very grateful for my mentors, friends, supporters, volunteers, and family. Until next time, THANK YOU!!!

What’s Next for Me?

As I heard numerous times at Parents Weekend at USC this week, I will “Fight on!”

I’m not sure what my next chapter will bring, but I am certain I will continue to try to make the world a better place for my family and community, and for those less fortunate than I am.

If I can be helpful to you, please let me know!