2025-11-14 16:03:00
Many startups focus on lead generation and outreach strategies, but there is often a hidden bottleneck that slows growth: the internal sales process. Inefficient processes can prevent leads from converting into paying customers, even when demand is strong. Recognizing and addressing these bottlenecks is critical for sustaining revenue growth. Without attention to internal workflows, even high-quality leads can stall, creating frustration for sales teams and missed opportunities that limit long-term scalability and business momentum.
Identifying Process Delays
Sales cycles in B2B environments involve multiple stakeholders, approvals, and technical evaluations. Delays often occur when proposals, contracts, or product information are not easily accessible. Teams may spend excessive time searching for resources or waiting for internal approvals, which frustrates prospects and increases the risk of lost opportunities. Data silos and fragmented communication between departments are common contributors to these slowdowns. These inefficiencies can also create inconsistencies in messaging, reduce customer confidence, and ultimately extend sales cycles.
Leveraging Technology for Efficiency
Implementing a centralized sales platform can dramatically reduce bottlenecks. Tools that integrate customer relationship management, proposal generation, and product documentation streamline workflows. For startups already using Microsoft Dynamics 365, incorporating ecommerce for Dynamics 365 can simplify order management and provide real-time visibility into inventory and pricing. Centralized platforms allow sales teams to respond faster to customer requests and reduce errors caused by manual data handling.
Aligning Teams and Processes
Internal alignment between sales, marketing, and operations is essential. Regular meetings to review workflows, identify pain points, and clarify responsibilities help teams act with cohesion. Establishing clear escalation paths for approvals and automating routine tasks allows sales staff to focus on relationship building and closing deals. Monitoring key performance indicators can reveal which steps in the sales process are causing delays and where improvements will have the greatest impact.
Startups that address internal bottlenecks gain a competitive advantage. Improving efficiency, leveraging integrated technology, and fostering cross-department collaboration allows teams to move leads through the pipeline more quickly. With fewer obstacles, sales staff can focus on driving revenue and building lasting customer relationships, ultimately supporting sustainable business growth. To learn more, look over the infographic below.
Photo by Microsoft Stock Images
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2025-11-12 18:11:57
This is an adapted excerpt from the introduction to Irresistible Change: A Blueprint for Earning Buy-In and Breakout Success by Phil Gilbert.
If ever there is a misnomer, it’s change management. It rarely causes change and it’s almost always mismanaged.
Why? The answer seems obvious to me: almost all leaders desiring change are businesspeople, but they never run their change initiatives like businesses.
Change should be regarded as a high-value-add product that deserves the same levels of resource support and operational rigor as any of your top-performing products. This means clear ownership, strategic leadership, and, above all, profit-and-loss accountability. Only when you treat change with this level of structure and discipline will you set it up for success.
In this model, change is your product, your organization is the marketplace, and its teams are your customers.
Change as a product must also be packaged and presented as a premium offering. No one values economy-class change. Only a platinum-tier solution will spark the excitement and customer demand required to drive widespread adoption of change, and have it stick.
That was my experience while leading IBM’s global transformation beginning in 2012, my colleagues and I helped thousands of interdisciplinary teams at IBM become more entrepreneurial, more agile, and more customer-focused.
For all those thousands of teams, we never had to mandate change, never had to beg anyone to join. In fact, we made the teams pay for our services. One-by-one, these IBM project teams utterly transformed their way of working because the entire design and execution of the program was based on delighting them and adding value at every touchpoint.
Those changes have stuck; they’ve become the cultural core for how IBM does business today.
For IBM’s global workforce of almost 400,000 people across 170 countries, we introduced radically different skills, practices, tools, and work environments. For another quarter million outside IBM, we provided learning tools and achievement certifications that enabled IBM clients to work more closely and productively with the company. Through Harvard Business School’s executive education program, countless others have since received certificates informed by our original change program.
The business results have been astonishing. IBM reduced overall product time-to-market by 50 percent. The company reduced the average time project teams needed to align on initial requirements by 75 percent and cut the time required for product development and testing by one-third. Employee engagement soared across virtually every level of the company (which I felt was the program’s most important strategic achievement). We created a program of irresistible change, one that people inside and outside IBM chose to opt into and benefit from.
Although it took us years to achieve these changes among the hundreds of thousands of IBM employees around the world, what made the crucial difference was the groundwork we laid in year one. During our third quarter, when we were still working with our first seven “customers,” we could already see how our program was poised for self-sustaining long-term success.
All change is hard. Change at scale is even harder. But the hardest challenge of all is making change at scale that sticks. Looking back today, long after I and most of my original core team have moved on, I get the most satisfaction from knowing how profoundly our changes stuck and flourished at IBM. The new ways of working we introduced in 2012 have since become so deeply rooted in IBM culture that they now constitute IBM’s everyday approach to product development, client service, and innovation.
The present is far more fragile than we often realize. Technology is an ever-present disruptor that has a way of commoditizing what once felt unique, driving a kind of Moore’s law-like acceleration into every corner of our daily workflows. Accepting this reality opens the door to a powerful truth: market leadership tomorrow will be determined by your ability to embrace and direct change today.
Change is inevitable—that much is clear. But what sets great organizations apart is the intentionality and speed with which they navigate change. Contentment with the way you work in the present is a setup for disaster in the future. A much healthier approach was once expressed to me this way: “We must always look at the status quo with disdain.”
Organizations that adopt this mindset at scale in the coming years will be the true winners—in the marketplace, within their communities, and even on the battlefield. In every type of industry, companies must use this disdain for the status quo to cultivate cultures of curiosity, innovation, and adaptability. Over time, these organizations will develop something far more valuable and powerful: an institutional predisposition–almost an instinct—for provoking continuous meaningful change.
Through our change program, we rediscovered and unleashed an entrepreneurial spirit that had been buried at IBM over the decades. Everything we achieved at IBM was just a prototype, a proof of concept for what comes next. What began more than a decade ago is now a sturdy template that I hope others will build on and make their own at any organization, of any size.
This adapted introduction from Irresistible Change: A Blueprint for Earning Buy-In and Breakout Success by Phil Gilbert is excerpted with permission from the publisher, Wiley. Copyright © 2025 by John Wiley & Sons, Inc. All rights reserved.
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2025-11-11 18:24:10
If you have never raised any money before, everything about the process might feel daunting. You will most likely get many, many no’s before you get a yes. I will not pretend that this can’t get demoralizing and exhausting. Fundraising can bring up a lot of fear of rejection and fear of failure. It can also feel uncomfortably like asking for a handout.
This can be especially true for founders who grew up in economically challenged households. They might have fears around how they are perceived by institutions of power. And they may feel that it’s demeaning to ask for money or that it reminds them of times of scarcity when their parents had to ask for assistance.
An uncomfortable feeling of pride can rear its head. I want to reassure you that in the process of getting loans, or grants, or investments, you are not asking for handouts. You are giving people the opportunity to partner with you in co-creation. You are someone else’s smart business decision.
If you are imagining that you will never be someone who can do this, I want to reassure you that you can—if you harness my three prospective Prosperity Principles.
A mistake people make in their fundraising mindset is thinking of it like a diet, or training for a marathon—something that they can grit their way through—until it’s over. However, funding is so intrinsic to founding—the words are only one letter apart. You have to become someone who pursues funding and revenue with the same energy you bring to other aspects of the venture.
The secret is incorporating the MAE (mindset, action, energy) framework to fundraising. It is what has made me a successful fundraiser—a combination of envisioning success, embodying that energy, and taking affirming actions through strong connection and by always putting myself out there. Then the universe takes over.
Some people are naturally comfortable in an endless cycle of fundraising. There are professional fundraisers who work for foundations and NGOs, and their entire job is asking people for money. We can learn a lot from them.
The key differentiator for professional fundraisers is that they are deeply motivated by what they are raising money for, and it is not themselves. Every day they are able to ask, ask, and ask again because they have a deep conviction that the money they are asking for will do good. You can harness this same strategy. You are not asking for yourself. You are not asking for this money because you want to be a rich CEO or because you want to be famous. You are asking for this money to have the opportunity to bring this idea to life. You are asking for the opportunity to serve your customers. You are asking for the opportunity to employ people in work they find meaningful and rewarding. You are asking for the opportunity to make a difference. And you are asking for the opportunity to return that money with interest. You are the Lorax speaking for the trees. You are speaking on behalf of your Deep Inner Why. You are its ambassador, and only you can help it get the oxygen it needs to catch fire.
Fear is not bad. Fear is the adrenaline that sharpens your focus and puts numbers in your mouth you weren’t even aware were in your brain. If you were asking for money with absolutely zero fear that you’d ever be able to pay it back, you’d be a cyborg. You are doing a big, brave, beautiful thing that not everyone is capable of, and your fear is here to remind you of that. It’s telling you that what you’re doing is important and you should take it seriously.
You might need to tap on that fear or ask your scared part what it needs to feel safe. This is an emotional process that brings up a lot for people, and we don’t need to pretend that it isn’t or that it doesn’t. By acknowledging the fullness of our experience, we can bring our whole self into the room, fear, and all.
When founders I mentor come to me feeling overwhelmed, and wondering if they really can achieve their goals, I take them through a focused process. I have seen how it can transform these feelings of fear and unworthiness into something you can love about yourself and make you even more the person who can and will carry out the great vision you hold for your life.
Sit in a comfortable, quiet place. Even though you may be having negative feelings, I want you to allow those feelings to recede for a moment and tune in to the feeling you’d like to embody. It
could be any of the 8 C’s—such as confidence, calm, courage— which are all very useful states to tap into.
Next, I’d like for you to envision if this state had a color, what would it be?
Open both palms in a receiving position on your lap and place the feeling you wish to embody in one of your hands. Use all of your senses: Visualize the feeling, hear it, taste it, touch it, and smell it. Imagine the color, shape, weight, temperature, and anything else interesting about this feeling you can conjure up. Get creative and curious. The more fun you can have, the better!
Now I’d like you to turn your attention to the other hand and do the same exercise but with the part of you that you would like to change. Maybe it feels hard and jagged, or sticky and clingy. Maybe it is hot to the touch. Or so cold it burns.
How old were you when you created this resistant part of yourself? Don’t overthink it, just say the first number that comes to mind.
Now conjure a memory from that age where you felt this feeling of resistance. What was being asked of you? Were you being asked to switch schools, go along with a divorce you hated, succeed in an area that was foisted on you?
Talk to that smaller, younger, innocent you that experienced that moment, what is it that the feeling of resistance wanted for you all along? Really try to have a conversation.
Your answer unlocks both feelings, the one in your left hand and the one in your right hand, to bring you new insights. Now clasp your hands together and thank that part for working tirelessly for you all these years to ultimately bring you the value you are holding in your other hand.
When we can learn to love all our parts, we can see our many facets working together for a greater good.
I leave you with this thought. Your prospectus is called an offering for a reason. You are offering the opportunity to partner with you. So shift from asking to offering, and watch the magic unfold.
This is an excerpt from Built on Purpose: Discover Your Deep Inner Why and Manifest the Business of Your Dreams by Betsy Fore. Copyright ©2025 by Betsy Fore. Used with permission of Harper Business, an imprint of HarperCollins. All rights reserved.
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2025-11-09 19:48:10
Every entrepreneur will tell you that startup life is demanding. From client meetings to admin, it never really stops. But when life throws unexpected curveballs, from health crises to personal losses, many entrepreneurs find themselves at risk of startup burnout.
Knowing how to recover during challenging times, without sacrificing wellbeing, is an essential life skill and it is extra important for entrepreneurs working towards long-term success.
In this article, we explore practical strategies for navigating life’s ups and downs while avoiding burnout. We hope that you find encouragement and practical advice that helps you on your journey.
From the outside, entrepreneurship can look like a fun adventure. You get to be your own boss, make your own hours, and take control of your life. And while all of that can be true, there are equally hard realities to running your own business.
For example, entrepreneurs often feel pressure from all sides – it’s up to them to make hard decisions. This can lead to long working hours, isolation, and feeling overwhelmed by responsibility. With few people to share their struggles with, these burdens can become overwhelming.
When major life events occur, such as illness, bereavement, relationship breakdowns, or even medical procedures like pregnancy termination, entrepreneurs can feel the pressure to power through and do it all. This never leads anywhere good and can cause the downfall of even the best business entrepreneurs. In fact, over 90% of start ups fail within the first five years. So, you must be proactive.
When you’re an entrepreneur and life hits hard, you can’t always stop work and take a break. So, you have to put protective measures in place that will give you the necessary space to recover, without letting your responsibilities spiral.
Here are some practical tips you can take action on, that will help you in your recovery:
After a difficult life event, many entrepreneurs feel the drive to jump straight back into work. But this is often counterproductive. True recovery begins when you give yourself the necessary space to heal. This might be just a few days, weeks, or more. But rest is critical.
There are a few ways you can give yourself time and space to heal, including:
Giving yourself time and space to heal is important and will help you recover properly before launching back into work.
Once you feel ready to properly return to work, it’s best to avoid jumping straight back into long, tiring days. Instead, establish a wellbeing-first routine. This means building wellbeing practices into your routine that are non-negotiable, such as:
Building these non-negotiables into your routine will provide you with a helpful structure during challenging times. It will also help mitigate entrepreneur burnout.
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If you have a team, it’s important to delegate effectively. Entrepreneurs often wear multiple hats, so the instinct to do everything yourself can be strong. However, doing it all is a recipe for startup burnout, particularly when you are going through personal challenges.
Learning how to delegate effectively is an essential skill and will help you manage effectively during a difficult time. Here are a few questions you can ask yourself:
When boundaries aren’t set, burnout can thrive. Protecting your time and energy is important. It’s also part of leadership.
Entrepreneurship can be a long, lonely road. Investing in relationships with people, such as therapists or coaches, who understand what you’re going through can be extremely rewarding, not to mention reassuring. Having the right support network can help you:
Having the right support network can help bridge the gap between life’s challenges and the practical aspects of running your business. We all need someone to talk to – even successful entrepreneurs.
If you’ve just experienced a challenging life event, you must prioritise your wellbeing. True recovery is about more than simply ‘getting back to normal’. It’s about creating a new kind of normal that prioritises sustainability over speed and pressure.
To set the stage for ongoing success, here are your next steps:
There is a famous quote from John C. Maxwell that perfectly summarises the importance of proactive recovery. We leave it with you in the hopes it provides drive and inspiration: “If you’re proactive, you focus on preparing. If you’re reactive, you end up focusing on repairing.”
Entrepreneurship is an exciting – but often lonely – journey. A lot falls on your shoulders. Therefore, you must take proactive steps to protect yourself from overworking and burnout. While never nice, sometimes the challenges life throws at you are reminders to take a step back, slow down, and recalibrate. Then you can return to work with a healthier, sustainable approach.
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2025-11-06 18:38:39
Choosing the right legal structure for your startup is a critical decision that can impact your business’s future success. This comprehensive guide explores 18 key considerations, drawing on insights from legal and business experts to help you make an informed choice. From tax implications to growth potential and investor expectations, understanding these factors will set your startup on the path to long-term success and compliance.
When helping clients choose the right legal structure, most gravitate toward the LLC because it provides liability protection with flexibility in taxation and management. That’s often the right call — but what many overlook is the operating agreement.
Think of the operating agreement as the law of the organization. It doesn’t just set out initial ownership — it governs how decisions are made, how profits are shared, and what happens if a partner wants out, contributes more down the road, or if relationships change (and they always do).
I’ve seen that the entity choice itself — LLC, corporation, or otherwise — is often a short-term decision based on liability and tax planning. But the real long-term safeguard is how well the governing documents anticipate the future. Planning for changes in business partners, contribution levels, and even unexpected disputes has proven far more important than most founders initially think.
So, while the LLC may be the right structure for many startups, don’t stop there — take the time to put the right operating agreement in place. It’s not just paperwork; it’s the roadmap that keeps your business on track as it grows.
Derek Colvin, Attorney, Waldrop & Colvin
When I launched both of my companies, I opted for a Delaware C-Corp structure. Initially, it seemed like the “default” choice because many startups choose this option, but I quickly learned why it’s significant.
The C-Corp structure allowed us to issue stock to team members and advisors, which has been invaluable for attracting talent in the early stages. It also positioned us favorably for investors and, eventually, acquisition discussions. Delaware, in particular, offers strong legal precedent and familiarity for VCs, thus reducing friction during deal negotiations.
What I didn’t fully appreciate at first was the importance of thinking years ahead, not just about the present. Forming the right legal structure isn’t merely paperwork; it shapes how you compensate people, how investors perceive you, and even how smoothly you can exit. In retrospect, I’m glad I made this decision early, because attempting to “fix” a structure later can be a costly distraction.
Eric Chebil, CEO & FOUNDER, Nest Navigate
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When we were setting up, choosing the legal structure initially felt like a formality — something to get out of the way so we could focus on building. However, as I delved deeper, I realized the decision would have ripple effects across funding, compliance, and even client trust. We evaluated options ranging from a lean proprietorship to a private limited company, and ultimately chose the latter because it struck the right balance between flexibility for growth and credibility with enterprise clients.
The consideration that proved more important than I initially thought was how the structure signaled legitimacy to potential partners and investors. At the time, I assumed tax treatment or operational convenience would be the biggest factors. But in practice, when we approached regulated industries like insurance and healthcare, being registered as a private limited company became a credibility marker. Clients were more comfortable signing multi-year contracts with us because the structure implied accountability and continuity.
That experience reshaped my perspective: the right legal structure isn’t just a back-office decision, it’s a strategic lever for trust and scalability. It taught me that in entrepreneurship, even foundational choices carry weight far beyond administration — they shape how the outside world perceives your seriousness.
Naresh Mungpara, Founder & CEO, Amenity Technologies
When my co-founder and I were setting up our agency, we opted for a Private Limited structure. The reason wasn’t glamour, but practicality.
At the time, it did feel like overkill compared to simpler options like LLP or partnership. However, once we started working with larger clients, especially enterprise tech firms, the credibility and compliance of a “Private Limited” entity made all the difference.
Procurement teams care about things like legal safeguards, invoicing compliance, and governance. Having the right structure upfront meant we didn’t lose time or deals proving our legitimacy.
The part I underestimated was how much the legal structure impacts long-term flexibility. With us two founders, the clarity around ownership, director responsibilities, and even something as basic as issuing equity to future employees would’ve been messy without the “Private Limited” framework.
It’s not the kind of decision you revisit often, so making it scalable from day one turned out to be one of the smartest moves we made.
Siddharth Vij, CEO & Design Lead, Bricx Labs
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When I set up my agency, I went with an LLC. What stunned me afterward was how much the tax structure shaped our growth trajectory. The flexibility to adjust how income was handled ended up giving us room to reinvest faster than I expected. Looking back, the paperwork was the easy part. The real impact came from how the structure influenced cash flow. My advice? Don’t just pick what looks simple on paper. Pick what sets you up to scale in the long run.
Cody Jensen, CEO & Founder, Searchbloom
When I launched my business, I chose an LLC because it struck the right balance — it protected me personally while offering flexibility with taxes and ownership. As the company grew, however, our needs changed. Bringing in partners and raising capital became priorities, and that’s when we transitioned to a corporation. Looking back, what really mattered wasn’t just picking the “perfect” structure at the start, but building in flexibility and being willing to pivot as the business evolved. That transition allowed us to scale without being boxed in by an early decision. My advice: choose a structure that works for your startup phase, but keep your long-term vision in mind. Be ready to adapt as growth brings new opportunities and challenges — because the proper legal foundation should evolve with your business, not hold it back.
Jared Weitz, Chief Executive Officer, United Capital Source
When we started, we raised investment immediately — so the legal structure had to align with venture expectations. This meant establishing a Delaware C-Corporation, not a Limited Liability Company (LLC) or any “lightweight” alternative. Investors prefer clean capitalization tables and standard governance, so our choice was less about taxes and more about alignment.
What I underestimated was how significantly the structure would shape the company later. Once you accept funding, governance is no longer theoretical — you become accountable to a board, to regular reporting, and to the way equity scales across a global team. The legal setup was less about protection and more about setting the rules of the game for growth.
Santiago Nestares, CoFounder, DualEntry
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I chose our legal structure after meticulously reading all legal entity structures and their formation documentation. I know that sounds a bit tedious, but to my surprise, it was well worth it.
While most people would turn to an attorney, I wanted to ensure I was knowledgeable about all the details myself. To my astonishment, I found I could file all formation documents on my own. This paid off in spades as I was able to save money and give myself the acuity I needed to know which legal structure was ideal for me.
I soon realized that each legal structure has its own strengths and weaknesses. I valued the legal protection of a corporation but also favored the lower tax ramifications of an S-corp. So I settled on a corporation with an S-Corp election. For me, it’s the perfect combination of both worlds.
Sean Gallagher, CEO / Founder, Gallagher Website Design
We chose an LLC when we started because it’s flexible for taxes and ownership. I initially thought protecting myself from liability would be the most important factor, but then I learned that how the structure would affect growth and partnerships was more crucial.
As we grew, the LLC allowed us to experiment with various revenue streams and bring contractors on board without having to discuss equity prematurely. I didn’t anticipate how much easier it would be to secure strategic partners. Many companies are cautious about legal risks and prefer working with structured entities. This helped us gain trust.
In retrospect, I believe that your structure’s ability to support long-term growth is the most important consideration, second only to liability protection.
Sebastian Hardy, Co-Founder, Market Your Architecture
Choosing the right legal structure for a startup is an important early decision because it affects taxes, fundraising, and flexibility. From my experience in digital marketing and growth strategies, I realized it’s crucial to select a structure that supports long-term growth. For example, since my business relies on client contracts and partnerships, setting up an LLC provided me with liability protection and was simple to manage in the beginning.
One aspect I didn’t fully consider initially was how the legal structure impacts credibility. While starting as an LLC worked well at first, switching to an S-Corp later helped me appear more professional when negotiating with larger clients. It also made taxes more efficient as the business grew, freeing up funds to invest in tools like Google Ads, Salesforce, and analytics platforms such as Looker Studio or Optimizely to improve operations and drive growth.
Ultimately, obtaining advice from legal and financial experts and choosing a structure that aligns with your goals is key. For professionals in industries like mine, balancing simplicity with the ability to scale and build trust with high-value clients is critical for long-term success.
Jose Angelo Gallegos, Founder & Growth Marketing Consultant, Jose Angelo Studios
We chose an LLC because it provided us with operational freedom while avoiding corporate formalities. The LLC seemed like an easy option at that time. The LLC structure proved essential for our business operations when we brought in investors and handled tax matters. The flexible structure of our LLC enabled us to maintain operational flexibility while our spa business expanded, and it simplified our operations when we began expanding.
The big surprise? The protection of personal assets through liability coverage turned out to be a major factor. The protection of your home from lawsuits becomes a significant concern after you begin welcoming customers through your doors.
Damien Zouaoui, Co-Founder, Oakwell Beer Spa
We chose an Aktiengesellschaft, or AG. It’s the Swiss equivalent of a corporation. We chose it because it gave us the best framework for our needs. We needed to raise capital, limit liability, and build credibility with international partners. So it was the most ideal fit.
A lot of discussions and considerations were also about the fact that an AG comes with significant obligations. You know, in terms of audits, shareholder reporting, and board oversight. These requirements add cost and time, and they forced us to build stronger internal processes earlier than I expected. So having that balance between credibility and compliance was the most important factor. Yes, it shapes your company’s perception in the eyes of investors, but it’s equally about how efficiently you can actually run the business day to day.
Mario Hupfeld, CTO and Co-Founder, NEMIS Technologies
The SAS structure (equivalent to an LLC in the US) became our choice because it offered flexibility through partner addition, liability protection, and simple fundraising processes. The business structure we chose brought unexpected changes to how investors viewed our company. The early-stage angel investor expressed his relief about our non-sole proprietorship status because it demonstrated our commitment to long-term operations.
The process of creating legal documents serves dual purposes, as it demonstrates our business commitment to investors. European investors evaluate companies through both their organizational structure and operational capabilities.
Vincent Carrié, CEO, Purple Media
When developing a medical practice, I selected a professional corporation due to the fact that liability and ownership regulations are of much greater concern in the healthcare sector than in many other businesses. Malpractice insurance applies in cases when it comes to covering clinical risks; however, the personal assets of the owner may be exposed if the structure is not appropriate. It did not occur to me that California law regarding physician ownership would influence virtually all financial decisions, including outside capital raising and partnership structure. A professional corporation shields the practice and ensures adherence to state medical board rules.
An aspect that has been overlooked is how retirement planning is directly related to the structure. In a professional corporation, I will be able to establish defined benefit plans or 401(k) plans that will enable large annual contributions, which could exceed $100,000 depending on income and years of service. This is a long-term financial instrument that simultaneously allows the flexibility to grow the practice or to attract associates on appropriate shareholder terms.
Gregg Feinerman, Owner and Medical Director, Feinerman Vision
One of the reasons why the S Corporation was chosen over LLC was the maximization of long-term growth and subsequent exit strategies. The first two considerations that many founders are concerned with are liability protection and pass-through taxation. The crunch point was found in the specifications of investor expectations and stock share distribution. Venture capital firms and other serious angel investors may have certain conditions that an S Corp structure can fit in a more organized manner, making the company a more attractive and less complex investment opportunity early on in its existence.
The selling of the business itself was one of the considerations that became much more important than expected. Section 1202 of the Internal Revenue Code offers a great deal of tax benefits to both the founder and the acquirer regarding the sale of stock, which is easily defined in an S Corp. The qualification of a small business stock exemption that can protect 100% of capital gains of up to ten million dollars in a way constitutes the company valuation and attractiveness in a strategic acquisition, and as such, is a core financial choice.
Kevin Heimlich, Digital Marketing Consultant & Chief Executive Officer, The Ad Firm
I had to choose between a sole proprietorship and an LLC structure. The latter would work, provided I wanted to grow the business to a significant extent. I chose sole proprietorship, as it allows me to do all my tax work easily (I do it alone with TurboTax) and my clients are still able to pay and work with our company easily. Should we need a more complex structure, we can always make adjustments as we go.
Ramona Jar, Lead SEO and Founder, SEO Rank Tracker
The right legal structure is not just about taxes or investment; it’s about long-term scalability and compliance.
When we were launching our healthcare IT startup, we initially chose a C-corp structure, believing it was the best way to attract investment. However, what I didn’t fully realize at the time was how deeply the legal structure would impact our compliance strategy. We were focused on securing funding but soon found that having a C-corp aligned with healthcare regulations, particularly HIPAA and data privacy laws, provided a much stronger framework for data protection and governance.
As a result, the C-corp structure gave us more control over intellectual property and allowed us to sign contracts with healthcare organizations more easily. The governance clarity ensured that everyone from investors to employees understood their roles in securing patient data. This decision played a big part in our ability to scale and secure partnerships.
For others facing similar decisions, my advice is to not only focus on the tax benefits or raising capital but to consider how the structure will affect your compliance and governance strategies. It’s critical to choose a structure that supports your long-term growth and legal obligations, especially in heavily regulated industries like healthcare. Consult with legal experts who can help you navigate both the business and regulatory landscapes.
Ultimately, understanding the full picture from taxation to compliance helps make the right legal choice that supports both growth and responsibility.
John Russo, VP of Healthcare Technology Solutions, OSP Labs
I went through this situation twice — the first time when co-founding my first tech consultancy, and the second when we decided to establish a division focused on AI programming, which also allowed us to help startups with AI projects.
The first time around, I was focused on the tax consequences and liability protection. Everybody talks about LLCs versus corporations, but what blinded me was how to structure ownership of the intellectual property. If you are building a consulting business focused on programming, in the end, your code, the processes you develop, and your relationships with clients become your most valuable assets.
I very nearly lost the first business we built because we didn’t correctly structure the IP assignment agreement which we designed, drafted, and signed. A cofounder who left claimed ownership of our proprietary SEO automation tool developed over 3 months. That was a horrible legal situation which cost us an attorney about $15,000 and 3 major contracts with clients.
The second time around, I was very keen to protect the ownership of all the IP mentioned above, and ownership where it was clear who owns what code, with a separate agreement for the lists of clients and also the project management framework we invented for our unique process. This ownership aspect was especially helpful when we branched out into AI/ML consulting because ownership of the intellectual property is exponentially more complicated when developing algorithms in machine learning.
What no one tells you is that your legal structure should mirror your growth potential and not your existing size. We originally selected a simple starting structure, but built in a required conversion down the road. When we were able to attract capital, and the excitement started, we were able to convert to a C-corp with our IP and contracts without having to reinvent the wheel each time.
The thing I didn’t expect the most was what an impact exit strategy has on the choice of structure. Even if you don’t think you would be bought/sell/exit/IPO for a long time, your legal structure matters as you start bringing on investors or doing a sale/transfer or merge with another company.
Rahul Jaiswal, Project Manager, Geeks Programming
Image by rawpixel.com on Freepik
The post 18 Important Considerations When Choosing a Legal Structure for Your Startup appeared first on StartupNation.
2025-11-04 15:17:36
Though the holiday season is the traditional time for spending, a feeling of caution, even dread, has formed a dark cloud over this time of extravagance.
Headlines about inflation, tariffs and government cutbacks are peppering the consciousness of the average consumer, resulting in cooler-headed, more conservative customers.
So, with tighter budgets, competition heats up. The question is how, despite these new pressures, a startup or small business can continue to benefit from the seasonal sales and win over new customers.
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Before we speculate on strategy, we need to understand who we are working with. What differentiates this year’s shopper from previous years’? To get some answers, we’ll refer to some relevant holiday shopping trends identified from customer data gathered by PissedConsumer.com.
As already touched upon, it is inflation and tariffs that are leading a shift in consumer sentiment and behavior. 64.9% of surveyed shoppers say that inflation will make a difference to their holiday spending, and 63% voice concerns that tariffs will price them out.
As expected, a budget adjustment is immediately apparent: 25% of those surveyed say that they plan to spend $1000+ on holiday shopping in 2025. This percentage is down from 30.3% the previous year.
How will these holiday shopping insights affect consumer spending? Well, this year’s holiday consumers will be more selective about what they buy and where they buy it. More shoppers will be placing emphasis on perceived value to justify purchases and retailer discounts as a way to make their dollar stretch further. Discounts, deals, and sales will hence attract more buyers than usual.
While online shopping is dominant, people are still seeing seasonal shopping as a physical event that they want to participate in, with most looking to shop both on and offline (65.3%). This tells us that despite the apparent diminishing relevance, the main street store still has a place in the holiday shopping schedule.
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There’s a mixture of methods attracting shoppers to discounts, too: 61% say they find bargains via online ads, direct emails (54.8%), and 44.2% locate a deal through flyers and other in-store ads or promotions. Even AI is squeezing itself into this category, with 10.8% they are utilizing ChatGPT et al. to help them plan out their holiday shopping. This data indicates that a multi-channel approach remains key to a strong advertising strategy.
There are many practical considerations for small businesses preparing for the fourth quarter. But before fussing over details, you need to set a solid foundation by establishing a good handle on the basics. This is a task that takes even the apparently mundane into account and emphasizes good planning and simple, efficient solutions.
We often hear the complaint that in our era of giant online retailers and mass monopolization, the personal connection has been lost, that interactions are now too impersonal and faceless. Small businesses are poised to make up for this.
With an emphasis on customer relationships rather than just sheer volume and market-leading prices, small retailers can develop an unmatched understanding of their customers’ wants and needs, tailor to the individual, and make every customer feel like their most important customer.
The two pillars of this approach are customer service and customer data. Listening and learning. A genuine understanding of the market for your product informs you of customer expectations and requirements, plus it gives your customer service operation the unrivaled position of being able to authentically place themselves in the customer’s shoes. The starting point for genuine conversations that form real, valuable connections.
Analysis of customer feedback can tell you a lot about a customer’s feelings, whereas data analysis will reveal the unspoken behaviors that tell us what customers want. Think of the purchasing patterns, what products and marketing they most frequently engage with. This and a variety of customer data points will help your business form an identity for each customer.
Such customer profiling will inform relevant product recommendations and, at scale, will help your brand cut the fat from your advertising and product catalog.
Make the most of this during the holiday season to reach out with the best offers for the right customers and ensure your discounts and sales reach those who’ll appreciate them most.
Christmas and the holiday season in general are a high-stress occasion for the average consumer. With all the organizing, budgeting, and other commitments, time becomes a precious commodity. Your advantage here is that, in many minds, cost is second to convenience.
As a customer, buying from your brand must be a swift, seamless, stress-free experience. An overly complicated UI, slow loading times, opaque policies, or any causes of confusion will try their patience, and even a little frustration could cause them to try their luck elsewhere.
Look at holiday spending and the customer journey through your customers’ eyes:
Do you accommodate all major payment options? The absence of their preferred method can be a dealbreaker for many shoppers.
Check your terms and conditions, particularly around tariffs, warranties, shipping, and returns. Are they straightforward, clear, and unambiguous? You ideally want to word these in a way that removes any possibility of misunderstanding or misinterpretation.
Is your pricing clear? Are all sales and discounts as they first seem? Is the browsed price the same as that at checkout? If taxes and tariffs push the price up, state this transparently and upfront. Don’t dump price shocks at the last minute and watch your cart-abandonment rates shoot up.
Price is not the only arena in which businesses can compete over the holidays. As a small business, you are more likely to specialize in a particular niche, and this is an opportunity to provide value without cutting prices.
A finer-tuned customer service is your competitive advantage. Smaller scale means you can better understand customer needs, offer more individual guidance, and possibly even get on first-name terms.
Be active and engage in the community that revolves around your niche. Tell the story behind your products or walk people through what makes your business different from the rest. Make a name for yourself as a trusted, reliable expert amongst peers, and you’ll develop a stable customer base that brings new trade through positive word of mouth.
Speedy, human help that treats customers like a friend rather than a statistic builds trust and a customer base that comes back again and again seeking expert advice and recommendations. This is particularly attractive to seasonal shoppers struggling to find a personalized gift for a friend or relative.
Many still see holiday shopping as an event they want to participate in, in person. If you have a physical storefront, capitalize on this. Encourage Instagram visibility and social media engagement with interesting and eye-catching themes and displays. Emphasize the value of the experience.
Inflation and tariffs pose a fresh challenge for small businesses this holiday shopping season, but the fact remains that more and more customers are seeking authenticity and connection in their purchases.
With massive online retailers dominating the market, anonymity has crept into the holiday shopping experience. For many people, this takes the spirit out of seasonal shopping; the sense of occasion and festivity is lost. This, combined with the needs of the increasingly values-driven consumer, places small businesses in a great position to step up and fill the gap.
Pursue this advantage and replace anonymity with a genuine connection. Instead of just supplying products at rock bottom prices, supply the meaning and sense of community that today’s consumers are lacking. Win the lasting loyalty of customers who appreciate what you do and will support your business long after the holidays are behind us.
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