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Startup founders, take note: Legal missteps can cost you equity, momentum and even your mission.
Startup founders, take note: Legal missteps can cost you equity, momentum and even your mission.

Technical.ly

time2 days ago

  • Business
  • Technical.ly

Startup founders, take note: Legal missteps can cost you equity, momentum and even your mission.

Having a lawyer to call is essential for founders, and they shouldn't wait until legal problems arise to establish that relationship. That theme underscored much of the 'Legal Trouble: Avoiding Common Startup Pitfalls' panel at the 2025 Builders Conference. Moderated by startup attorney Jeffrey Bodle of Morgan Lewis, the panel featured cautionary tales and practical advice from Baltimore-area founders Matthew Hayes and Shari Bailey of Unmanned Propulsion Development and Laila's Gift, respectively. 'Think of building a business like building a home,' Bailey said. 'If you skip inspections until the end, you might have to tear out the foundation. Do things right and tight up front.' Both founders stressed the long-term costs of early legal shortcuts. Hayes recounted how, in the absence of experienced startup attorneys in the rural Maryland area where he used to work, he leaned on a family member who practiced real estate law. It didn't go well because they didn't focus on startup law. 'On the business side, specialists help; generalists don't,' he said. Bailey agreed, especially for anyone navigating both for-profit and nonprofit structures, as she does. Laila's Gift throws birthday parties for children with special needs while also developing a tech product to support the same community. Her guiding principle? Document everything. She referenced a GMP (good manufacturing process) term, 'document control,' that she believes transcends any industry. 'Keep records of everything, with revision control,' she said. 'Meeting minutes, decisions, training — store them in a central repository everyone can access so the history doesn't live in one person's head.' Match your legal partner to your growth trajectory Even if they're not ready to retain a lawyer, entrepreneurs have options for services and platforms that can provide some guidance, even if they don't replace the expertise of a skilled attorney. 'If you have funding, hire an attorney,' Bailey said. 'If not, services like Rocket Lawyer can help … volunteers can help nonprofits; ChatGPT is a great starter — not a finisher.' Hayes said much of his early legal documentation was taken from other firms' NDAs. 'All my NDAs were basically copied from other companies, nobody's going to sue over that,' he said. Plus, if you want legal protection that scales with your business, be sure to think long-term. 'You don't necessarily have to pick one firm forever,' Morgan Lewis' Bodle said, 'but if you expect to grow like a weed, choose a firm that can scale. Businesses evolve. Keep a few candidates in mind and revisit as you grow.' Attorneys in the audience added practical tips: avoid hourly billing in favor of modest retainers plus success fees; keep documentation simple but tight; and vet your lawyer as thoroughly as you would a cofounder. Bodle urged founders to use tools like AngelList's Stripe Atlas, Clerky or Gust for standard startup documents, and to approach legal work incrementally. 'Term sheets also keep costs low: Until you agree on key terms, nobody wastes time drafting the rest,' he said. The panel closed with a reminder from Hayes that even in the face of adversity, founders can still shape their outcomes. During the pandemic, he co-founded a nonprofit — Southern Maryland Loves You — and worked with local volunteers to create an FDA-authorized mask-sanitizing system that hospitals clamored to use. But it was 'messy,' per Hayes. His congressional representative allegedly leaked his FDA support letter to a competitor's lobbyist, so he quickly learned to operate more discreetly. Key lessons from that experience? 'Have a lawyer you can call; keep communication open; be someone people don't want to sue,' Hayes said, 'and don't work with people who sue.'

How lawmakers are regulating real-world AI in 2025
How lawmakers are regulating real-world AI in 2025

Technical.ly

time4 days ago

  • Business
  • Technical.ly

How lawmakers are regulating real-world AI in 2025

When it comes to regulating artificial intelligence, lawmakers are stuck between needing to act quickly and needing to get it right. That tension was at the heart of 'What Does Real-World AI Regulation Look Like?', a panel discussion at the 2025 Builders Conference featuring Pennsylvania state Rep. Napoleon J. Nelson, Wilmington Councilmember James Spadola and John Hopkins-Gillespie, director of policy at responsible AI governance startup Trustible AI. From autonomous vehicles to AI-powered teaching bots, use cases are outpacing public understanding — and policymakers are struggling to catch up. 'When tech starts moving at speeds that make tech people's eyes go crazy,' Nelson said, 'How do we create governance structures that work for something that's going so darn fast?' Nelson advised lawmakers not to 'chase headlines' by relying on simplified narratives or a surface-level understanding of AI to decide when and how to legislate. In fact, legislators should purposely craft 'reactive' legislation to the tech, according to Spadola. 'I want to prevent people from getting hurt as much as we can,' Spadola said, 'but I think it's good to let the market do what the market's going to do and figure out how we deal with the negative ramifications.' Companies are handling this by setting their own guardrails in the absence of formal regulation, according to Hopkins-Gillespie, whose company helps organizations implement AI governance. 'The last thing you want to do is be in the news for having something go wrong because you didn't have a safety check or quality assurance process in place,' Hopkins-Gillespie said. Real use cases, real policy gaps Throughout the discussion, the legislators shared real-world examples of approaching AI in their current roles. Spadola sees the tech as a net positive and has already put it to work in Wilmington. The city already uses AI-powered tools like ShotSpotter and license plate readers for public safety. 'I look at AI as: How can we help run the municipality better?' Spadola said. Nelson pointed to a recent case in Pennsylvania involving cyber charter schools applying to use AI-powered chatbots as teachers. The applications were denied, but not because the technology was deemed unsafe. The government just didn't have policies in place to fully audit its quality. 'We don't have a real framework to understand, well, what's our policy on hallucination rates? And how many times can a chatbot say something that's incorrect that then violates a contract?' Nelson said. 'We don't know.' The need for education through collaboration The panelists agreed on the need for stronger collaboration between tech companies, policymakers and communities. Hopkins-Gillespie called for more proactive education, where the industry side breaks down what legislators should know about AI. 'Most policymakers are not experts on these things,' he said. 'And so, where there are gaps, where there are opportunities for us to educate and show some of the work we're doing, where some things have worked, where some things haven't gone great.' The collaboration also extends to the relationship between constituents and elected officials. Spadola recommended that constituents build relationships with their legislators before asking for help navigating AI-related concerns. 'Form a relationship now,' he said. 'It's just better to get known now than before you come with a problem or an ask.' In the meantime, AI regulation is a waiting game. The policy bottleneck, according to Nelson, is political, not technical. 'It doesn't take seven years to actually codify, to write good policy,' Nelson said. 'It takes seven months to write good policy, and the other six and a half years is just fighting over it.' This shouldn't stop businesses from still embracing it in the meantime, though. 'Don't fear the technology,' Hopkins-Gillespie said. 'Learn about the technology.'

How to hone your startup pitch for every audience — and avoid ‘show-up-and-throw-up'
How to hone your startup pitch for every audience — and avoid ‘show-up-and-throw-up'

Technical.ly

time4 days ago

  • Business
  • Technical.ly

How to hone your startup pitch for every audience — and avoid ‘show-up-and-throw-up'

The most important pitch you give might not be to a VC — it could be a future hire, customer or fellow founder. At the 'Honing Your Pitch: For Sales, Investors & Employees' panel at the 2025 Builders Conference, three seasoned leaders shared what makes a pitch resonate and what many founders still miss. Moderated by Barry Wright, an executive at healthtech company Noom, the panel featured Ben Bartolome, vice president of commercial banking for startups at J.P. Morgan; Naza Shelley, founder and CEO of matchmaking startup CarpeDM; and David Cummings, founder and CEO of Atlanta Ventures. 'You'll pitch about 10,000 times in the life of your startup,' Wright said. 'Every conversation is a pitch.' One takeaway from panelists is to be deeply prepared, but share just enough to spark interest without overwhelming your audience. Shelley, whose startup has raised more than $2 million, said preparation is crucial, especially for underrepresented founders. 'Asking for money is hard and harder for minorities, and triply so for Black women,' Shelly said. 'If I don't know an answer cold, I'm written off as incompetent. I learned I must be super prepared, know every detail, anticipate every question.' Cummings, a co-founder of marketing automation company Pardot and early Calendly backer, offered a hard-won lesson from his early years as a founder. 'I suffered early from the 'show-up-and-throw-up,'' Cummings said. 'I wanted them to know every detail and got lost in word salad. Now, I simplify. Give just enough, with a hook, so they say, 'Tell me more.' If I overwhelm them, I fail.' Even when a pitch doesn't go as planned, there's often lessons to take away. Bartolome, a former fintech founder, recalled a fumbled B2B negotiation that cost him a six-figure deal and valuable traction. 'They wanted 5% equity for early partnership,' he said. 'I refused. We haggled over single-digit points and lost a six-figure [annual recurring revenue] deal plus strategic momentum. In hindsight, that 5% was nothing compared with the benefit.' How to handle the talkative investor What do you do when a potential funder won't let you speak? 'Be excited,' Shelley advised. 'They're engaged. Flow with their questions, weave your points into answers. Your goal is their decision, not your slide order.' The real objective of a first investor meeting is simply to get a second one, Cummings added. However, founders should also be mindful of their most limited resource: time. Chasing too many investors can be a distraction. If a startup can grow through customer revenue, more VC calls don't always mean more value, according to Bartolome. 'Some founders schedule 200 VC calls,' Bartolome said. 'If customer revenue can fund you, focus there. A few high-probability VC calls beat 200 low-probability ones.' To avoid dragging out fruitless conversations, Bartolome recommended clarity. '[Ask] timeline questions,' he said. ''When do you issue term sheets? 'When should I follow up?' If they can't answer, treat it as a soft no.' Sometimes, though, getting a fast 'no' from a potential investor can be a blessing in disguise, according to Shelly. 'I push to 'no' quickly,' Shelly said. 'After one to two meetings, I ask check size, timeline, [if they] lean yes or no. If no, I drop them to annual updates.' Tailor your pitch to the audience — while staying authentic Founders tend to perfect their pitch for investors, but often forget how crucial it is when talking to potential employees. This, too, is a kind of sale. 'I ask about capacity and willingness for early-stage hours,' Shelly said. 'Be explicit so misfits self-select out.' Regardless of who a founder is pitching to, authenticity matters. Panelists emphasized that a founder's story isn't just about the company – it's about why they are the right person to solve a problem. 'My founder-market fit is personal. I'm building for women like me,' Shelley said. 'That authenticity carries across investors, employees, customers.' By the end of the panel, Wright offered a final takeaway of lessons for the audience. 'Simplify your pitch, tell authentic stories, push for clear timelines,' Wright said, 'and be intentional in every conversation.'

AI tools won't replace storytellers, but these 7 tools can make the job easier
AI tools won't replace storytellers, but these 7 tools can make the job easier

Technical.ly

time4 days ago

  • Business
  • Technical.ly

AI tools won't replace storytellers, but these 7 tools can make the job easier

AI won't replace human storytellers, but it can supplement their approach for a wider reach. That was the underlying message of 'AI Tools for Storytelling: For Places, Companies & Brands,' a panel at the 2025 Builders Conference that drew professionals across civic, nonprofit and private sectors. Moderated by GateCheck Studio's Sean Blanda, the conversation featured Alanah Davis, Baltimore's chief storyteller, and Tim Kulp, chief innovation officer at Mind Over Machines. While AI is a powerful assistant, storytelling still needs human direction, according to the panelists. Plus, there are certain things the tech just can't replicate. 'Don't go to [AI] for expertise,' Kulp said. 'You have the expertise. Go to it to help you format and formulate that expertise.' At Mind Over Machines, Kulp's team uses Microsoft 365 Copilot and a custom agent called 'Katie' to track projects, extract useful case studies and support onboarding. For teams just starting with AI, Kulp warned against treating it as a low-stakes sandbox. 'You want to have a use case that is actually going to create the impact and change,' Kulp said, 'and that's not going to happen if everybody has a mindset of 'that's just the playground.'' Start with tasks like repurposing content or summarizing transcripts, he said, and measure against manual workflows to establish return on investment. That clarity helps with internal buy-in, builds momentum and encourages what he called 'the curious mindset.' Using AI doesn't mean losing authenticity As Baltimore's first chief storyteller, Davis faces the challenge of sharing narratives from a city government that's still catching up with 21st-century tech. In her role, Davis wants to use AI tools like for transcription, but municipal IT restrictions often block or delay access. That means finding workarounds, like off-platform Google accounts or partnering with freelancers who can use the tools she can't. Still, Davis remains optimistic about what AI can offer, particularly when it comes to outreach. 'I think it's important that we're learning it and that we're not afraid of it,' she said. 'I like to embrace it, even though I'm all about connection, humanity [and] authenticity.' The AI tools worth your time So what tools are worth checking out? The panelists shared a short list. But keep in mind, panelists said: Whether you're working in city hall or a startup accelerator, the human component is irreplaceable. 'In order to do this, you have to have good storytelling already,' Davis said. 'Get the basic thing right before you extend it.'

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