Scaling is where things get real. The scrappy hacks that got you to product-market fit start to crack, your calendar explodes, and suddenly everything feels important. Growth is exciting, but without the right systems, people, and leadership in place, it can get messy fast. The Road To: Scaling Smarter is your no-fluff guide to growing without breaking what you’ve built. Pulled from Startup Boston Week sessions, this series dives into the real questions founders face at scale

When early-stage founders rush to hire, sign customers, or collaborate with partners, legal paperwork rarely feels urgent. But according to startup attorneys Alicia Dorner  and Beth Lamontagne  of Foley & Lardner , those early decisions can quietly shape (or jeopardize) the long-term survival of a young company. In a conversation with Startup Boston, both attorneys pointed to a recurring pattern: founders don’t intentionally skip legal steps. They just underestimate how much

At Startup Boston Week, one panel challenged a piece of startup folklore that refuses to die: that the best startups are simple ones. Moderated by Suvojit Ghosh , Founder and CEO of FYELABS, Inventing the Future: Building Startups with Technically Complex Products  brought together founders who are building far beyond apps, dashboards, and lightweight software tools. Instead, they’re tackling problems rooted in healthcare, human dignity, animal health, and behavioral science

If you’re building a Seed or Series A SaaS company, your board doesn’t want a wall of numbers. They want five crisp signals that show your growth engine, your path to profitability, and your runway to keep going. The trick is not to collect more data points. It’s to ruthlessly pick the right few, define them once, and manage them every single week (at least every month). And in periods when you fall short of any of your key target thresholds, gather the data to understand why

January in Boston doesn’t ease you into the year - it hits the ground running. From deep tech and AI to founder support, community building, and capital connection, the first month of the year is packed with events worth putting on your radar if you’re building, backing, or supporting startups in Greater Boston. Startup Boston is anchoring the month with four community-powered experiences: Mentor Matching for Early-Stage Founders (Jan 12)  - An intimate, mentor-driven session

When a startup survives nearly two decades, you pay attention to how.  That was the energy in the room during Startup Boston Week’s session Market-Proof Your Startup: Thriving Through Shifts and Trends .  The conversation paired David Chang , founding member of TBD Angels , with Chris Savage , co-founder and CEO of Wistia , a Boston-born company known for raising venture capital, and then purchasing the startup back from investors to scale independently. Savage and Chang unpa

“If only I had time to pause and reflect”  responded a collaborator to the idea of a reflection & goal-setting activity around the upcoming New Year. And honestly, that reaction is common. When we’re moving fast, reflection is often the first thing to slip off the calendar. But what happens when we don’t take the time to reflect on what’s working and what isn’t? We stick with unhelpful habits. We allow interpersonal friction to build and fester. And we miss out on opportuniti

If you had asked me two years ago whether I’d be building an AI startup focused on IRB and research compliance, I would’ve probably laughed. Like many founders, I didn’t intentionally walk into this space. I simply kept running into the exact same pain point over and over again - and eventually, the problem became too loud to ignore. I spent years in academic and medical research across Harvard Medical School, MGH, Mount Sinai, and Northwell Health. No matter the institution

Securing pre-seed funding as a first-time founder is about far more than having a great idea, it’s about telling a story investors believe in, selling a vision for what’s possible, and proving you’re the one to build it. Before traction, before revenue, and often before a finished product, founders must learn how to communicate clarity, confidence, and potential in a way that cuts through the noise. Recorded live at Startup Boston Week 2025, this session breaks down how to cr

Launching a startup means making dozens of decisions with limited time, money, and knowledge. Few decisions feel as high-stakes as the legal ones. How should you form the business? Who should own what? What if you’re still working a full-time job while building your idea on nights and weekends? At Startup Boston Week 2025, Touchstone Strategic Law’s managing partners Michael Perez and Elizabeth Norman  pulled back the curtain on the legal choices that define a company’s found

A founder’s calendar can quickly become a graveyard of “great intentions.” You start the year energized by ambitious goals, but the day-to-day reality of investor meetings, customer fires, and operational demands can pull you in every direction except forward. During our recent panel on designing a founder schedule  for the year ahead, six practical frameworks surfaced as the tools founders actually rely on to stay focused, accountable and resilient. If you’re ready to trade

I’ve sat in too many leadership meetings that erupt into shouting matches. Smart, capable founders interrupt, talk over, or tear each other down. Someone storms out. Someone else shuts down, a peacekeeper tries to smooth it all over. Everyone walks away convinced they were the reasonable one. This is what unproductive conflict looks like in startups: raw emotion, high stakes, and zero recovery. It isn’t because people don’t care — it’s because communication is a learned skill

Inside Startup Boston & City of Boston’s year-end planning panel With just weeks left before the calendar turns over, Startup Boston and the City of Boston brought together three seasoned founders - each with wildly different entrepreneurial journeys - to tackle a deceptively simple question: How should founders actually plan their 2026 schedule? Moderated by Startup Boston  founder Stephanie Roulic , the conversation quickly moved beyond calendars and time-blocking. What unf

Massachusetts isn’t just leading in climatetech - it’s building the playbook for how innovation and policy can work together to solve the planet’s hardest problems. Here, cutting-edge research meets forward-thinking legislation, and founders have access to an unparalleled network of universities, accelerators and investors that know what it takes to bring climate solutions from lab to market. With more climatetech startups per capita than any other state and a coordinated str

Scaling a startup doesn’t just test your business model, it tests you as a leader. The skills that helped you build your company from the ground up aren’t always the ones that will carry it forward. As teams expand, decisions get more complex, and expectations rise, founders must evolve from doers to leaders - learning to communicate vision, delegate effectively, and build systems that empower others to excel. Recorded live at Startup Boston Week 2025, this session dives into

Last night, we hosted our third FounderConnect with CIC’s Social Impact Program, bringing together founders and resource partners who are fueling Boston’s startup community. The energy in the room was incredible, founders connecting with accountants, HR pros, developers and advisors all focused on one shared goal: helping startups build smarter, stronger, and faster. Each company and organization represented offers a different piece of the startup puzzle - from tax and legal

Author: Derek Fieldhouse, Customer Success Manager, Fidelity Private Shares Raising your first or second round is a major milestone that you want to be prepared for. It is perhaps the first time you will have outside investors scrutinizing every detail of your company, especially your cap table. A messy or inaccurate cap table can slow down diligence or even scare investors away. As someone who’s worked with numerous companies through their seed rounds, I’ve seen how a clean

Authored by: Matt Shrimpton & Bob Baker, Partners at Peak Corporate Counsel Startups need money, and usually a lot of it. Building a team and an MVP can get expensive, and at some point in the lifecycle of most startups, they will seek outside capital. Most of these raises will involve equity financing – receiving money in exchange for a percentage of ownership in the company. Investors will want to put their money in a business which provides a unique and valuable product o

As your startup scales, your board can either accelerate your growth, or slow it down. The difference often comes down to how well you manage the relationship. From aligning expectations and preparing for tough conversations to turning board feedback into strategic advantage, this session dives into what it really takes to build and lead a high-performing board. Recorded live at Startup Boston Week 2025, this discussion explores the evolving role of the board through the lens

Being an underrepresented founder in the startup world often means navigating invisible barriers while building something new. But it also comes with a deep well of resilience, creativity, and community. At Lifting as We Climb, with Startup Boston and City of Boston, founders and investors came together to talk candidly about the realities of representation - and how we can all play a role in building a more inclusive ecosystem. The panel last night featured Farah Hussain  (E