The Entrepreneur's Champion: Jay Norris' Lifelong Mission to Empower Entrepreneurs
Jay Norris has always been on the move. It's not just a personality trait; it's a philosophy, a way of living, and a responsibility he carries. As the founder and CEO of GUESST, a software and AI-powered platform designed to empower small to medium-sized businesses (1-500 employees), Norris is more than a tech entrepreneur. He's a champion for the people who bring vibrancy and authenticity to our neighborhoods, restaurateurs, boutique owners, and local service providers, the backbone of American life.
"I want to be a momentum for people," he says. "Positive momentum."
That momentum began in Lafayette Park, a mixed-use neighborhood in downtown Detroit, where Norris grew up. His childhood was surrounded by small businesses: delis, art galleries, nightclubs, and family-run restaurants that pulsed with creativity and independence. He didn't recognize it then, but he was witnessing something profound. "I saw freedom in their eyes," he recalls. "They woke up every day, providing for their families on their own terms. That nourished me."
That early exposure to entrepreneurship planted a seed that would grow through decades of experience across marketing, entertainment, and real estate. In the music industry, Norris helped legends bring their artistic visions into the world. Later, he transitioned into commercial real estate, where he represented tenants, a less common path in a field largely dominated by landlord advocates. Yet even there, he felt pulled toward helping people realize their dreams.
"There is a common thread," he explains. "I have always found myself alongside people birthing ideas into the world. Whether it was an artist, a restaurant owner, or a tech founder, I want to help give structure to that dream, to help them bring it to life."
That mission is deeply personal. Norris' father, who worked in banking and provided small business loans, laid another layer of foundation. "I didn't think much about it until later in life," he says, "but now I realize that I'm following in his footsteps, just with software instead of signatures."
This ethos led to the creation of GUESST , an AI platform that tracks retail and restaurant leases and performance data in real time. By identifying key business metrics and making them actionable, GUESST helps entrepreneurs stay in business longer and make smarter decisions. "I couldn't keep consulting one client at a time," Norris says. "Technology was the only way to scale my impact."
But he's clear: GUESST is just one tool in a much larger toolkit.
"GUESST is one cylinder in a hundred-cylinder engine," he says. "It's a great entry point, but I want to surround myself with other AI and software solutions that address different pain points small and medium businesses face."
The road has not always been smooth. As a tenant rep in Manhattan, Norris saw firsthand how quickly businesses could disappear. He says. "That broke me. These people had mortgaged their homes, put everything into their dreams. And the system didn't care."
He pitched the idea of tenant support services to his former brokerage firm and was told to "Just sell." That was not enough. He left and began building an advisory group focused on long-term sustainability for small and medium businesses, now a fully fledged strategic advisory firm, Lifestyle Equities . GUESST emerged from that desire to not just place businesses in spaces, but help them stay there.
The deeper driver behind all this is community. "I walk down streets and see my friends, dry cleaners, tailors, cooks gone. That's not just a business loss. That's a loss of culture," Norris says. "They are what I call neighborhood amenities. They bring the spirit to a place."
That spirit is what he wants to protect. Through his podcast "Visionary's " where he interviews high-impact entrepreneurs, to inspire up-and-coming entrepreneurs. In his leadership roles as Co-Chairman of the Manhattan Chamber of Commerce and board member of Startup Westport , Norris is constantly connecting dots between people, resources, capital, and opportunity.
"I'm a connector," he says. "That's my gift. Whether it's bringing a merchant and a banker together or tracking KPIs to measure impact, I'm using software to scale what I have been doing my whole life: helping people build their dreams."
He sees every introduction as a potential bridge, and every bridge as something that should be measured. "We connect people, but do we ever track if it worked? That's what we are building now: the systems that let us improve every time we help someone," Norris says.
At the heart of it all is belief. Belief in small business as the American dream. Belief in technology as a tool, not a replacement. And belief in community as the foundation of a healthy economy.
"Who wants to live in homogeneous communities? I know I don't," he says. "I don't think we are meant to. Small businesses are the beating heart of our communities."
For Jay Norris, moving forward is about lifting others as he goes, one entrepreneur, one idea, one connection, one community, at a time.
Try Our AI Features
Explore what Daily8 AI can do for you:
Comments
No comments yet...
Related Articles
Int'l Business Times
18 hours ago
- Int'l Business Times
The Entrepreneur's Champion: Jay Norris' Lifelong Mission to Empower Entrepreneurs
Jay Norris has always been on the move. It's not just a personality trait; it's a philosophy, a way of living, and a responsibility he carries. As the founder and CEO of GUESST, a software and AI-powered platform designed to empower small to medium-sized businesses (1-500 employees), Norris is more than a tech entrepreneur. He's a champion for the people who bring vibrancy and authenticity to our neighborhoods, restaurateurs, boutique owners, and local service providers, the backbone of American life. "I want to be a momentum for people," he says. "Positive momentum." That momentum began in Lafayette Park, a mixed-use neighborhood in downtown Detroit, where Norris grew up. His childhood was surrounded by small businesses: delis, art galleries, nightclubs, and family-run restaurants that pulsed with creativity and independence. He didn't recognize it then, but he was witnessing something profound. "I saw freedom in their eyes," he recalls. "They woke up every day, providing for their families on their own terms. That nourished me." That early exposure to entrepreneurship planted a seed that would grow through decades of experience across marketing, entertainment, and real estate. In the music industry, Norris helped legends bring their artistic visions into the world. Later, he transitioned into commercial real estate, where he represented tenants, a less common path in a field largely dominated by landlord advocates. Yet even there, he felt pulled toward helping people realize their dreams. "There is a common thread," he explains. "I have always found myself alongside people birthing ideas into the world. Whether it was an artist, a restaurant owner, or a tech founder, I want to help give structure to that dream, to help them bring it to life." That mission is deeply personal. Norris' father, who worked in banking and provided small business loans, laid another layer of foundation. "I didn't think much about it until later in life," he says, "but now I realize that I'm following in his footsteps, just with software instead of signatures." This ethos led to the creation of GUESST , an AI platform that tracks retail and restaurant leases and performance data in real time. By identifying key business metrics and making them actionable, GUESST helps entrepreneurs stay in business longer and make smarter decisions. "I couldn't keep consulting one client at a time," Norris says. "Technology was the only way to scale my impact." But he's clear: GUESST is just one tool in a much larger toolkit. "GUESST is one cylinder in a hundred-cylinder engine," he says. "It's a great entry point, but I want to surround myself with other AI and software solutions that address different pain points small and medium businesses face." The road has not always been smooth. As a tenant rep in Manhattan, Norris saw firsthand how quickly businesses could disappear. He says. "That broke me. These people had mortgaged their homes, put everything into their dreams. And the system didn't care." He pitched the idea of tenant support services to his former brokerage firm and was told to "Just sell." That was not enough. He left and began building an advisory group focused on long-term sustainability for small and medium businesses, now a fully fledged strategic advisory firm, Lifestyle Equities . GUESST emerged from that desire to not just place businesses in spaces, but help them stay there. The deeper driver behind all this is community. "I walk down streets and see my friends, dry cleaners, tailors, cooks gone. That's not just a business loss. That's a loss of culture," Norris says. "They are what I call neighborhood amenities. They bring the spirit to a place." That spirit is what he wants to protect. Through his podcast "Visionary's " where he interviews high-impact entrepreneurs, to inspire up-and-coming entrepreneurs. In his leadership roles as Co-Chairman of the Manhattan Chamber of Commerce and board member of Startup Westport , Norris is constantly connecting dots between people, resources, capital, and opportunity. "I'm a connector," he says. "That's my gift. Whether it's bringing a merchant and a banker together or tracking KPIs to measure impact, I'm using software to scale what I have been doing my whole life: helping people build their dreams." He sees every introduction as a potential bridge, and every bridge as something that should be measured. "We connect people, but do we ever track if it worked? That's what we are building now: the systems that let us improve every time we help someone," Norris says. At the heart of it all is belief. Belief in small business as the American dream. Belief in technology as a tool, not a replacement. And belief in community as the foundation of a healthy economy. "Who wants to live in homogeneous communities? I know I don't," he says. "I don't think we are meant to. Small businesses are the beating heart of our communities." For Jay Norris, moving forward is about lifting others as he goes, one entrepreneur, one idea, one connection, one community, at a time.
Local Germany
21 hours ago
- Local Germany
'System feels unfair': The struggle of getting German citizenship as a freelancer
Kathryn, an American citizen who works as a freelancer, moved to Germany more than 15 years ago. Since then, she's faced years of bureaucratic challenges: paying for tax audits and lawyers, receiving incomplete or unhelpful information from immigration authorities and navigating a system that feels stacked against her. Staying in Germany as a freelancer, she said, has never been easy – or cheap. Now, she's beginning her application for German citizenship, a process that's proving to be just as burdensome. Marcelo, a freelance artist from Brazil, has faced similar challenges. After living in Germany for seven years, Marcelo began the process of applying for German citizenship in October last year and has been going back and forth with the immigration authorities ever since. 'I would say that there is quite a discriminatory practice between freelancers and people who have a regular nine-to-five job,' Marcelo said. Both Kathryn and Marcelo have asked to be identified only by their first names because they are still in the process of applying for citizenship. Working as a freelancer does not disqualify you from becoming a German citizen, but as Kathryn and Marcelo have both found, it can make the process slower, more expensive and more confusing. Advertisement Freiberufler visa makes freelance work possible for expats The Freiberufler visa allows non-EU citizens to be self-employed or work as freelancers in Germany for three years at a time. It's an attractive option for many foreign residents, as the visa offers a way to work in Germany without a full-time employment contract. To receive this visa, applicants must show letters of intent from clients and evidence they can support themselves financially. READ ALSO: The compete guide to getting a freelance visa in Germany As a reminder to become a German citizen, all applicants are generally required to have been living in Germany for at least five years, have a long-term residence permit or permanent right of residence, pass a citizenship test and speak German at a B1 level. But for foreign freelancers who hope to one day become naturalised, it's important to understand how working as a freelancer can complicate the process of attaining citizenship. Advertisement Additional paperwork, additional expenses Because most freelancers have several employers, rather than just one, documenting taxes and income can get complicated. Freelancers applying for citizenship in Berlin must submit a Prüfungsbericht , or an audit report conducted by a tax professional, according to the ServicePortal Berlin website . Freelancers must also submit their last Steuerbescheid , or tax assessment, and a tax clearance certificate, or Steuerunbedenklichkeitsbescheinigung. In contrast employees with salaried jobs need only to submit their employment contract, their last six months of salary statements and a statement from their employer concerning the duration of the employment, the ServicePortal website says. German immigration authorities can be quite meticulous when reviewing freelancers' financial documents, and even minor discrepancies between invoices and bank statements can raise red flags. In the more than 15 years Kathryn has spent as a freelancer, she said she's run into all kinds of issues reporting her taxes and income. As an example she once received a €23 refund on a Deutsche Bahn ticket. When she later submitted a bank statement that included that refund, the clerk reviewing her documents accused her of receiving compensation for unreported freelance work with Deutsche Bahn. Advertisement Citizenship comes at a cost Another challenge freelancers face when applying for citizenship is the heavy cost burden. Just getting a Prüfungsbericht can sometimes cost upwards of €1,000. Over the course of the application process, Marcelo has already paid around €2,000 for lawyers and tax professionals, as well as for official translations of documents. 'I had to ask for help from my parents, because I couldn't do it myself,' Marcelo said. 'So I do feel like it's something that is quite prohibitive.' Kathryn estimated she'd spent between €5,000 and €10,000 annually on freelance-related expenses since moving to Germany. That includes lawyers, tax professionals, document translations and insurance, not to mention all the hours of income she's lost. 'Honestly, it's not felt worth it. I mean, I kept fighting for it. I kept staying here,' she said. 'But I would say altogether, it has not been worth it.' Freelancers say German bureaucracy isn't made for them A lack of transparency and clarity from immigration authorities is another complaint foreign freelancers have voiced. Kathryn said she has never been told exactly how much money she needs to make in order to prove she can support herself. Even though options like the Freiberufler visa make freelancing a viable path for international residents, some freelancers still say the system doesn't feel like it's set up for them. 'German society is not really geared towards being a freelancer,' Marcelo said. 'You are supposed to be here really in a like nine-to-five job contract…that's what they want.' READ ALSO: Five hard truths about starting out as a freelancer in Germany Kathryn said she and her husband, a German national who also freelances, have considered leaving Germany altogether because of these bureaucratic challenges. Kathryn has looked into relocating to countries including the Netherlands, New Zealand and Senegal – all of which were friendlier to freelancers than Germany is, she said. 'Why is it so hard here?' Kathryn said. 'I just find there's not a lot of clarity here.' Have you had similar experiences applying for German citizenship as a freelancer. We want to hear from you. Share your story in the comments section or email us at news@
Int'l Business Times
a day ago
- Int'l Business Times
Not Quite A Victory Lap: Rethinking The US–China Trade Agreement
The newly announced trade deal between the United States and China is being described as a breakthrough moment in what has been a rocky and prolonged economic standoff. Both sides are scaling back tariffs and promising a more stable trading relationship. But look a little deeper, and the picture becomes less about resolution—and more about damage control. This agreement isn't the end of a conflict. It's more like a timeout. Tariffs Rolled Back, But Still High One of the headline changes is that U.S. tariffs on Chinese goods are being lowered to 55%, while China has agreed to reduce its own import duties to around 10%. While these are improvements compared to the highs seen during the peak of the trade war, they're still steep by historical standards. As reported by CNBC, the long-term consequences of earlier tariff hikes—including supply chain disruption and sourcing shifts—have already reshaped how U.S. companies operate. Many manufacturers have moved operations to countries like Vietnam, Mexico or India. The latest deal doesn't undo that shift, and many industry analysts argue it likely won't. The Rare-Earth Factor: Strategic Access or Strategic Risk? A central pillar of the agreement is China's pledge to expand exports of rare-earth elements—critical materials used in electric vehicles, wind turbines, and most modern electronics. On the surface, this appears to be a major win for the U.S., which has been grappling with access to these minerals due to export restrictions and a lack of domestic processing capability. But the deal also underscores just how dependent the U.S. remains on China for these resources. According to a report by The Australian, China's decision to allow rare-earth exports comes with no long-term guarantees and no change in control over the global supply chain. In effect, the U.S. is securing short-term access without reducing its strategic vulnerability. No Real Fix for the Structural Divide What this agreement does not include is just as important as what it does: No binding framework on intellectual property protection No enforcement mechanism for subsidy transparency No tariff freeze beyond the next 90 days This lack of structural depth raises questions about the durability of the deal. As reported by Finance Magnates, many economists see the announcement as a political maneuver designed to calm markets ahead of further negotiations, rather than a resolution to long-standing economic tensions. What It Means for Businesses and Consumers For American consumers, this deal might bring a modest reprieve from price hikes on certain imported goods—especially electronics, tools, and industrial inputs. For businesses, the effects are more nuanced. Companies that rely on Chinese components could benefit from reduced tariffs, but the continued volatility and short time horizon (tariffs are up for reassessment in 90 days) mean long-term planning is still risky. Supply chain diversification efforts that began during the height of the trade conflict are unlikely to reverse. Instead, many firms may continue sourcing from alternative markets to hedge against future uncertainty. Final Word: A Deal, Yes—But Not a Resolution This deal represents a cooling-off period, not a cure. It de-escalates tensions and offers temporary relief, but leaves the deeper economic rifts between the U.S. and China unresolved. With additional trade discussions scheduled with India and the EU in July, and tariff reviews just weeks away, this agreement is best seen as a fragile pause—not a permanent peace.
