Being an Entrepreneur | February 2026
- Chris Herbert
- 7 hours ago
- 10 min read
Featured in this Post
Get Started with Cowork: Claude's Desktop Agent for Knowledge Work
Anthropic has released Cowork, a new feature that lets Claude handle complex, multi-step tasks on your computer while you step away. Instead of responding to prompts one at a time, you can describe an outcome and come back to finished work—formatted documents, organized files, synthesized research, and more.
Practical use cases range from organizing messy folders and processing receipts into expense reports, to combining research from multiple sources into polished summaries, extracting action items from meeting transcripts, and turning rough notes into finished documents or presentations. Claude can also create Excel spreadsheets with working formulas and PowerPoint decks—not just rough drafts that need fixing.
With scheduled tasks, Claude can complete recurring work automatically—something that isn't possible in regular chats. Think of weekly report preparation, file cleanup routines, or regular data processing that currently eats up your time.
For entrepreneurs and small business owners exploring AI tools, Cowork offers a new model worth testing: hand off the task, let Claude work in the background, and review the output when it's done.
Whether it delivers meaningful productivity gains will depend on your workflow and willingness to experiment. The feature is available for paid Claude plans (Pro, Max, Team, Enterprise) on Claude Desktop for macOS and Windows.
Date: February 2026 | Source: Get started with Cowork
Succession Planning: Why Delaying Costs More Than Money
For many Canadian business owners, succession planning gets pushed off—not because they don't care, but because they care deeply. The conversations involve identity, family dynamics, mortality, and legacy.
But delaying doesn't make these hard decisions go away; it forces families to rush through them during a crisis.
The emotional barriers are real: transition means confronting aging and retirement, risking conflict over ownership and roles, and navigating complexity across taxes, governance, and estate planning. Optimism bias compounds the problem—it never feels urgent until it suddenly is.
Agricultural succession coach Maggie Van Camp adds a deeper dimension, particularly for farmers: "Letting go of control of something that's so integrated into our DNA, our bodies, our brains, our hearts and yes our egos, feels like voluntarily chopping off your own arm. Trusting someone—even the most capable successor—to care for and even change this part of you, takes bravery. So we avoid it, using the excuse of being too busy, until we are forced by a life event to make quick, reactive changes."
The financial consequences of waiting are concrete under Canadian tax law. On death, all capital property triggers a deemed disposition at fair market value, creating an immediate capital gains tax bill.
Delays can mean missing the lifetime capital gains exemption (up to $1,250,000 on qualifying small business shares, indexed to inflation starting in 2026), losing estate freeze opportunities that shift future growth to the next generation, increased probate costs, and forced asset liquidation under unfavourable terms.
Van Camp reframes the entire conversation: "Proactively planning with incremental shifts allows the outgoing generation to help slowly strengthen what we are giving to the next generation. It also gives us the time to build new strengths that we're going to need in the third phase of our lives—things like new purposes, relationships and financial security. Succession is not giving something up; it's strengthening what you're giving, and stepping into what's next with intelligence, intention and love."
For farmers over 50 in eastern Ontario, Van Camp recommends the Groundworks succession peer group funded by AAFC, starting in March with limited registration. Contact karla.rahn@agriskmanagers.ca to sign up.
Date: 2026 | Source: Delaying succession planning can cost you more than money
Is Your Venture Capital Industry Quietly Leaving Billions in Economic Value on the Table?
Startup Genome poses a provocative question for ecosystem builders: if you had significant capital to deploy into your innovation ecosystem, should you prioritize producing more investable founders or developing a mature venture funding industry?
The reality is you need to do both. If you succeed in producing investable founders while your venture capital ecosystem continues to underperform, you will inevitably lose talent to more mature markets. If you build a robust VC ecosystem without sufficient deal flow, you will see capital flow elsewhere.
The analysis identifies three systemic weaknesses plaguing most venture ecosystems globally.
First, an unclear definition of "maturity"—leaders celebrate growth in startup creation and capital deployed, but lack a strategically useful view of where the system is structurally constrained.
Second, a missing theory and toolkit for change—even when gaps are identified, policymakers struggle to translate diagnosis into practical roadmaps, frequently applying interventions that fail to address the right problem.
Third, lack of public sector intentionality—governments have dozens of levers to strengthen private market capacity but rarely design them as part of a coherent system.
The AI era makes this even more urgent. AI-Native startups have quite different funding characteristics than other tech startups. As AI lowers the cost of company formation and accelerates scaling timelines, the speed and quality of early-stage investment judgment becomes more decisive. AI is compressing funding timelines—ecosystems without fast, high-quality capital decision-making will fall behind.
For Canadian entrepreneurs and policymakers, this analysis reinforces a familiar challenge: developing investable founders means little if local capital can't move quickly enough to back them before they relocate to more mature markets.
Date: February 24, 2026 | Source: Is your venture capital industry quietly leaving billions in economic value on the table?
Picking Board Members for Early-Stage Startups: What Actually Matters
Mark Le Dain, CRO at Fuelled, offers blunt advice for founders assembling their first boards: prioritize trust, practical help, and financial backstop over prestigious names or "strategic advice."
His four criteria are straightforward.
First, pick individuals where there is a high amount of trust—delivering bad news quickly, without taking time to explain or soften, is the best way to actually get useful advice when it's most needed.
Second, board members should be able to actually help you grow; strategic advice is overrated, while lots of effective board members are making active intros to customers, partners, and investors.
Third, experience should be relevant—pattern recognition saves a lot of time.
Fourth, and critically, you need someone on the board who can write a cheque if you need it, personally or through their fund. If you have less than six months of runway, you can lose all leverage on everything from fundraising to mergers without someone who can step in fast.
Le Dain notes he's "seen lots of great companies that wouldn't exist if there wasn't someone in the early days that did exactly this—gave them a line of credit in 24 hours, topped up a round personally that had remained open to extend runway."
The comments add nuance.
Robert Abalos argues that formal board members before Series A make little sense: "Keep your seed board nominal—your management team, maybe an angel who wrote a check. The last thing a nimble startup hustler needs is board bureaucracy."
Graeme Harrison warns against picking people based on social profile, noting that anyone with enough clout to matter may be hesitant to go all-in if they perceive reputational risk.
For founders, the takeaway is clear: build a board that can act, not just advise.
Date: February 2026 | Source: Mark Le Dain on LinkedIn
What to Know About Equity Take-Outs: Turning Property into Business Growth
If your business owns commercial real estate, you may be sitting on untapped capital. An equity take-out allows you to access the value already built up in your commercial property and reinvest it strategically in your business, without giving up ownership or taking on outside investors. BDC explains how the financing mechanism works and when it makes strategic sense.
The concept is straightforward: as your property increases in market value and the mortgage gets paid down, the difference between the two becomes available equity.
For example, say your commercial property is worth $5 million and you still owe $1.8 million on the mortgage. You refinance into a new $2.3 million mortgage. The new loan pays off the old one, and you walk away with $500,000 in cash. Your mortgage payment increases, but you now have capital to deploy. You still own the property—you just owe more on it.
Business owners commonly use equity take-outs to expand operations, buy equipment or technology, acquire another business, strengthen cash flow during seasonal fluctuations, or support ownership transitions.
The key advantages: you keep full control with no equity dilution, gain flexible use of funds, and often secure better terms through longer amortization periods and competitive rates.
The critical question before proceeding: "Ask yourself whether the investment you're making will generate a return that is higher than the cost of borrowing," advises Stuart Freeman, Manager at BDC Business Centre.
In practical terms, if you pull out $500,000 at a 6% interest rate, you're paying roughly $30,000 annually in additional interest—that's your cost of capital. Your investment needs to earn more than that. If new equipment generates $80,000 in additional annual profit, or an acquisition adds $120,000 in cash flow, the math works. If the funds cover operating losses or speculative ventures with no clear payback, you're taking on debt without a path to repay it.
The test: can you project incremental revenue, cost savings, or efficiency gains that comfortably exceed your new debt servicing costs?
Date: January 8, 2026 | Source: What to know about equity take-outs: Turning property into business growth
Rural Renaissance: Why Canada's Economy Is Outgrowing Its Big Cities
What began as crisis has become opportunity. A Rural Renaissance is reshaping where Canadians live, how they work, and how Canada rebuilds the industrial and human foundations of national resilience.
This argument from Joseph Fournier, a senior fellow at the Frontier Centre for Public Policy, challenges the long-held assumption that economic dynamism belongs exclusively to major urban centres.
The case builds on two major underlying trends: the erosion of urban lifestyles and the rise of a knowledge-based economy. Anyone who has lived in a major urban area in the past 50 years has seen the quality of life constrained as housing prices exploded. In Toronto, for example, urban infrastructure is clearly not keeping pace with population growth—driving commutes that used to take 30 minutes are now snarled traffic nightmares that take 90 minutes or more.
As this new economy begins to deepen its roots, the capacity to spread the more attractive qualities of urbanity throughout the countryside could make rural Canada—with its clean air and safe, affordable communities—an attractive option for a new generation.
For entrepreneurs, this shift presents both opportunity and strategic imperative: rural regions offer lower operating costs, quality of life advantages, and—particularly in areas like Grey-Bruce with nuclear, agriculture, and energy assets—proximity to growth sectors that don't require downtown office towers. The takeaway is clear: build where the fundamentals support you, not where convention dictates.
Date: February 1, 2026 | Source: Rural Renaissance: Why Canada's Economy Is Outgrowing Its Big Cities
This Gen Z Pair Built a $34M Startup in Canada, Only to Move to U.S.
Two Gen Z founders—neither of them Canadian—built Internet Backyard while studying in Vancouver, raising $4.5 million USD at a $34.5 million CAD valuation before relocating to San Francisco to scale.
Co-founder Mai Trinh is an international student from Vietnam; her co-founder Gabriel Ravacci is from Brazil. Their platform, Gnomos, automates billing and financial metrics for data center operators still managing finances on spreadsheets.
After incorporating in Delaware, Internet Backyard closed its funding round ($4.5M USD) in just one week. By contrast, across all of Western Canada in Q1 2025, total pre-seed funding was just $3 million USD.
Trinh cited Canada's fragmented regulatory landscape and slower customer adoption: "US customers are more comfortable piloting. In Canada, procurement cycles are slower, and people wait for regulatory certainty."
While this story highlights ecosystem gaps, it also raises a question for Canadian policymakers and educators: are we investing enough in developing homegrown entrepreneurial talent?
Canada's universities and accelerators attract ambitious founders from around the world—but if the ecosystem can't retain them, the same barriers will push Canadian-born founders south too. "You have all these micro funds that really want to support first-time founders," Trinh noted. "But because they don't have enough capital, it becomes very hard."
The priority should be building pathways for Canadian entrepreneurs to launch, fund, and scale here—not just training talent for export.
Date: January 27, 2026 | Source: This Gen Z pair built a $34M startup in Canada, only to move to U.S.
Y Combinator Reverses Decision, Will Invest in Canadian-Domiciled Startups Again
Y Combinator's decision to restore Canada to its list of accepted countries—after quietly removing it late last year—offers relief for Canadian founders, but also exposes a deeper vulnerability in the domestic startup ecosystem.
The original change would have forced Canadian startups to reincorporate in the U.S., Cayman Islands, or Singapore to participate in the world's most influential accelerator.
That a single Silicon Valley institution could send shockwaves through Canadian tech highlights how reliant the ecosystem remains on external validation and capital.
The reversal came after sustained backlash, with investor John Ruffolo summarizing the outcome bluntly: "I guess being a fucking pain works." Yet the debate revealed a divided community—some argued YC was simply formalizing what ambitious founders already do, while others pushed back on the narrative that redomiciling is necessary to attract capital. Former Panache Ventures partner Chris Neumann noted that "virtually every US VC is willing to invest in a Canadian-domiciled company."
For entrepreneurs, this episode raises strategic questions beyond incorporation. Only 32.4 percent of Canadian-led high-potential startups created in 2024 were headquartered in Canada.
The underlying gaps—limited early-stage risk capital, slower procurement cycles, and weaker global signaling from domestic programs—persist. Canadian founders should advocate for stronger homegrown alternatives while recognizing that building for global markets often means navigating ecosystems beyond our borders.
Date: February 5, 2026 | Source: Y Combinator reverses decision, will invest in Canadian-domiciled startups again
Comments